Pyridyl oxycarboxylic acid oxime derivative and preparation method therefor, weeding composition and application thereof

ABSTRACT

The invention relates to the field of pesticide technology, and in particular a type of pyridyloxy carboxylic oxime derivative, preparation method, herbicidal composition and application thereof. The pyridyloxy carboxylic oxime derivative is represented by formula I, 
     
       
         
         
             
             
         
       
     
     wherein, A, B each independently represent halogen, or alkyl or cycloalkyl with or without halogen; C represents hydrogen, halogen, alkyl or haloalkyl; Q represents halogen, cyano, cyanoalkyl, hydroxyalkyl, amino, nitro, formyl, alkyl with or without halogen and the like; R 1  and R 2  independently represent hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, acyloxy, alkylthio, or unsubstituted or substituted aryl, etc.; M represents nitro or NR 3 R 4 . The compound has excellent herbicidal activity and higher crop safety, especially good selectivity for key crops such as rice.

TECHNICAL FIELD

The invention relates to the field of pesticide technology, and inparticular a type of pyridyloxy carboxylic oxime derivative, preparationmethod, herbicidal composition and application thereof.

TECHNICAL BACKGROUND

Weed control is one of the most important links in the course ofachieving high-efficiency agriculture. Various herbicides are availablein the market, for example, DE2335349A1, GB1418979A, U.S. Pat. Nos.3,761,486, 3,755,339 and the like disclose a series of compoundsrepresented by the general formula

and application thereof as herbicides. However, scientists still need todo continuously research and develop new herbicides with high efficacy,safety, economics and different modes of action due to problems such asthe growing market, weed resistance, the service life and economics ofpesticides as well as people's increasing concern on environment.

INVENTION CONTENTS

The present invention provides a type of pyridyloxy carboxylic oximederivative, preparation method, herbicidal composition and applicationthereof. The compound has excellent herbicidal activity and higher cropsafety, especially good selectivity for key crops such as rice.

The technical solution adopted by the invention is as follows:

A pyridyloxy carboxylic oxime derivative represented by formula I,

wherein, A, B each independently represent halogen; or alkyl orcycloalkyl with or without halogen;

C represents hydrogen, halogen, alkyl or haloalkyl;

Q represents halogen, cyano, cyanoalkyl, hydroxyalkyl, amino, nitro,formyl; alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio,alkylcarbonyl, alkoxycarbonyl, alkylaminoalkyl or alkoxyalkyl with orwithout halogen; or unsubstituted or substituted aryl, heteroaryl,arylalkyl or heteroarylalkyl;

R₁ and R₂ independently represent H, halogen, cyano, nitro, alkyl,haloalkyl, alkenyl, cycloalkyl, alkoxy, acyloxy, alkylthio,unsubstituted or substituted aryl, unsubstituted or substituted benzyl,unsubstituted or substituted heteroaryl, unsubstituted or substitutedaryloxy, unsubstituted or substituted arylthio, unsubstituted orsubstituted heteroaryloxy, unsubstituted or substituted heteroarylthioor the group represented by the formula of —COR₅, wherein, R₅ representsalkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, alkenoxy, cycloalkoxy,alkylthio, alkenylthio, cycloalkylthio, unsubstituted or substitutedbenzyl, unsubstituted or substituted aryl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted aryloxy, unsubstituted orsubstituted heteroaryloxy, unsubstituted or substituted arylalkyloxy,unsubstituted or substituted heteroarylalkyloxy, unsubstituted orsubstituted arylalkylthio, unsubstituted or substitutedheteroarylalkylthio, unsubstituted or substituted benzylthio,unsubstituted or substituted arylthio, unsubstituted or substitutedheteroarylthio, or amino which is optionally substituted by alkyl, acyl,acyloxy, unsubstituted or substituted aryl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted arylalkyl or unsubstituted orsubstituted heteroarylalkyl; or R₁ and R₂ are linked to form a 5- or6-member saturated or unsaturated ring;

M represents nitro or NR₃R₄, wherein R₃ represents H; alkyl, alkenyl oralkynyl optionally substituted by 1-2 R₁₁; —COR₁₂, nitro, OR₁₃, SO₂R₁₄,NR₁₅R₁₆, N═CR₁₇R₁₈, alkylcarbamoyl, dialkylcarbamoyl, trialkylsilyl ordialkylphosphono; R₄ represents H; alkyl optionally substituted by 1-2R₁₁; or —COR₁₂; or NR₃R₄ represents N═CR₂₁NR₂₂R₂₃, N═CR₂₄OR₂₅; or a 5-or 6-membered saturated or unsaturated ring with or without oxygen atom,sulfur atom, or other nitrogen atom, which is unsubstituted orsubstituted by 1-2 groups independently selected from the groupconsisting of halogen, alkyl, alkoxy, haloalkoxy, alkylthio,haloalkylthio, amino, alkylamino, dialkylamino and alkoxycarbonyl;

wherein R₁₁ independently represents halogen, hydroxy, alkoxy,haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino,alkoxycarbonyl; or unsubstituted or substituted aryl or heteroaryl;

R₁₂ represents H, alkyl, haloalkyl, alkoxy, phenyl, phenoxy orbenzyloxy;

R₁₃ represents H, alkyl, haloalkyl, phenyl, benzyl or CHR₃₁C(O)OR₃₂; R₃₁represents H, alkyl or alkoxy; R₃₂ represents H, alkyl or benzyl;

R₁₄ represents alkyl or haloalkyl;

R₁₅ represents H, alkyl, formyl, alkylacyl, haloalkylacyl,alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl;R₁₆ represents H or alkyl;

R₁₇ represents H, alkyl; or phenyl that is unsubstituted or substitutedby 1-3 groups selected from the group consisting of halogen, alkyl andalkoxy; R₁₈ represents H or alkyl; or N═CR₁₇R₁₈ represents

R₂₁, R₂₄ each independently represent H or alkyl;

R₂₂, R₂₃ each independently represent H or alkyl; or NR₂₂R₂₃ representsa 5- or 6-membered saturated or unsaturated ring with or without oxygenatom, sulfur atom, or other nitrogen atom;

R₂₅ represents alkyl.

Preferably, A, B each independently represent halogen; or C1-C8 alkyl orC3-C8 cycloalkyl with or without halogen; C represents hydrogen,halogen, C1-C8 alkyl or halo C1-C8 alkyl; Q represents halogen, cyano,cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, amino, nitro, formyl; C1-C8alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C1-C8 alkoxy,C1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8alkylamino C1-C8 alkyl or C1-C8 alkoxy C1-C8 alkyl with or withouthalogen; or unsubstituted or substituted aryl, heteroaryl, aryl C1-C8alkyl or heteroaryl C1-C8 alkyl;

R₁ and R₂ independently represent H, halogen, cyano, nitro, C1-C8 alkyl,halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8acyloxy, C1-C8 alkylthio, unsubstituted or substituted aryl,unsubstituted or substituted benzyl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted aryloxy, unsubstituted orsubstituted arylthio, unsubstituted or substituted heteroaryloxy,unsubstituted or substituted heteroarylthio or the group represented bythe formula of —COR₅, wherein, R₅ represents C1-C8 alkyl, halo C1-C8alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8 alkenoxy,C3-C8 cycloalkoxy, C1-C8 alkylthio, C2-C8 alkenylthio, C3-C8cycloalkylthio, unsubstituted or substituted benzyl, unsubstituted orsubstituted aryl, unsubstituted or substituted heteroaryl, unsubstitutedor substituted aryloxy, unsubstituted or substituted heteroaryloxy,unsubstituted or substituted aryl C1-C8 alkyloxy, unsubstituted orsubstituted heteroaryl C1-C8 alkyloxy, unsubstituted or substituted arylC1-C8 alkylthio, unsubstituted or substituted heteroaryl C1-C8alkylthio, unsubstituted or substituted benzylthio, unsubstituted orsubstituted arylthio, unsubstituted or substituted heteroarylthio, oramino which is optionally substituted by C1-C8 alkyl, C1-C8 acyl, C1-C8acyloxy, unsubstituted or substituted aryl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted aryl C1-C8 alkyl orunsubstituted or substituted heteroaryl C1-C8 alkyl; or R₁ and R₂ arelinked to form a 5- or 6-member saturated carbocyclic ring;

M represents nitro or NR₃R₄, wherein R₃ represents H; C1-C8 alkyl, C2-C8alkenyl or C2-C8 alkynyl optionally substituted by 1-2 R₁₁; —COR₁₂,nitro, OR₁₃, SO₂R₁₄, NR₁₅R₁₆, N═CR₁₇R₁₈, C1-C8 alkylcarbamoyl, di-C1-C8alkylcarbamoyl, tri-C1-C8 alkylsilyl or di-C1-C8 alkylphosphono; R₄represents H; C1-C8 alkyl optionally substituted by 1-2 R₁₁; or —COR₁₂;or NR₃R₄ represents N═CR₂₁NR₂₂R₂₃, N═CR₂₄OR₂₅; or

that is unsubstituted or substituted by 1-2 groups independentlyselected from the group consisting of halogen, C1-C8 alkyl, C1-C8alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino,C1-C8 alkylamino, di-C1-C8 alkylamino and C1-C8 alkoxycarbonyl;

wherein R₁₁ independently represents halogen, hydroxy, C1-C8 alkoxy,halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8alkylamino, di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl; or phenyl,naphthyl,

that is unsubstituted or substituted by 1-3 groups selected from thegroup consisting of halogen, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxyand nitro;

R₁₂ represents H, C1-C18 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, phenyl,phenoxy or benzyloxy;

R₁₃ represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl, benzyl orCHR₃₁C(O)OR₃₂; R₃₁ represents H, C1-C8 alkyl or C1-C8 alkoxy; R₃₂represents H, C1-C8 alkyl or benzyl;

R₁₄ represents C1-C8 alkyl or halo C1-C8 alkyl;

R₁₅ represents H, C1-C8 alkyl, formyl, C1-C8 alkylacyl, halo C1-C8alkylacyl, C1-C8 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl orbenzyloxycarbonyl; R₁₆ represents H or C1-C8 alkyl;

R₁₇ represents H, C1-C8 alkyl; or phenyl that is unsubstituted orsubstituted by 1-3 groups selected from the group consisting of halogen,C1-C8 alkyl and C1-C8 alkoxy; R₁₈ represents H or C1-C8 alkyl; orN═CR₁₇R₁₈ represents

R₂₁, R₂₄ each independently represent H or C1-C8 alkyl;

R₂₂, R₂₃ each independently represent H or C1-C8 alkyl; or NR₂₂R₂₃represents

R₂₅ represents C1-C8 alkyl;

the term “aryl” refers to phenyl or naphthyl; the term “heteroaryl”refers to an aromatic ring group containing 3 to 6 ring atoms and isoptionally fused via benzo ring, 1 to 4 heteroatoms in the ring atomsbeing selected from oxygen, nitrogen and sulfur, for example,

which is optionally substituted by at least one group selected from thegroup consisting of halogen, nitro, cyano, thiocyano, hydroxy, carboxy,mercapto, formyl; phenyl, benzyl, benzyloxy or phenoxy that isunsubstituted or substituted by at least one group from the groupconsisting of halogen, alkyl and alkoxy; alkyl, alkenyl, alkynyl,cycloalkyl, cycloalkylalkyl, OR″, SR″, -alkyl-OR″, -alkyl-SR″, COR″,COOR″, COSR″, SOR″, SO₂R″, OCOR″ or SCOR″ with or without halogen; andamino or aminocarbonyl substituted by one or two groups selected fromthe group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkylalkyl, phenyl, benzyl, benzyloxy, phenoxy, COR″, COOR″, SO₂R″and OR″;

R′ each independently represents hydrogen, nitro, hydroxy, amino; oralkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkoxyalkyl,alkoxycarbonyl, alkylthiocarbonyl, alkylsulfonyl, alkylsulfonylalkyl,alkylcarbonyl, alkylcarbonylalkyl, alkylacyloxy, alkylamino,alkylaminocarbonyl, alkoxyaminocarbonyl, alkoxycarbonylalkyl,alkylaminocarbonylalkyl, trialkylsilyl or dialkylphosphono with orwithout halogen;

R″ each independently represents hydrogen, alkyl, alkenyl, alkynyl,cycloalkyl or cycloalkylalkyl.

More preferably, A, B each independently represent halogen; or C1-C6alkyl or C3-C6 cycloalkyl with or without halogen;

C represents hydrogen, halogen, C1-C6 alkyl or halo C1-C6 alkyl;

Q represents halogen, cyano, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl,amino, nitro, formyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6 alkylamino C1-C6 alkyl or C1-C6 alkoxy C1-C6 alkylwith or without halogen; or unsubstituted or substituted aryl,heteroaryl, aryl C1-C6 alkyl or heteroaryl C1-C6 alkyl;

R₁ and R₂ independently represent H, cyano, C1-C6 alkyl, halo C1-C6alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 acyloxy,C1-C6 alkylthio, unsubstituted or substituted aryl, unsubstituted orsubstituted benzyl, unsubstituted or substituted heteroaryl,unsubstituted or substituted aryloxy, unsubstituted or substitutedarylthio, unsubstituted or substituted heteroaryloxy, unsubstituted orsubstituted heteroarylthio or the group represented by the formula of—COR₅, wherein, R₅ represents C1-C6 alkyl, halo C1-C6 alkyl, C2-C6alkenyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C2-C6 alkenoxy, C3-C6cycloalkoxy, C1-C6 alkylthio, C2-C6 alkenylthio, C3-C6 cycloalkylthio,unsubstituted or substituted benzyl, unsubstituted or substituted aryl,unsubstituted or substituted heteroaryl, unsubstituted or substitutedaryloxy, unsubstituted or substituted heteroaryloxy, unsubstituted orsubstituted aryl C1-C6 alkyloxy, unsubstituted or substituted heteroarylC1-C6 alkyloxy, unsubstituted or substituted aryl C1-C6 alkylthio,unsubstituted or substituted heteroaryl C1-C6 alkylthio, unsubstitutedor substituted benzylthio, unsubstituted or substituted arylthio,unsubstituted or substituted heteroarylthio, or amino which isoptionally substituted by C1-C6 alkyl, C1-C6 acyl, C1-C6 acyloxy,unsubstituted or substituted aryl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted aryl C1-C6 alkyl orunsubstituted or substituted heteroaryl C1-C6 alkyl; or R₁ and R₂ arelinked to form a 5- or 6-member saturated carbocyclic ring;

M represents nitro or NR₃R₄, wherein R₃ represents H; C1-C6 alkyl, C2-C6alkenyl or C2-C6 alkynyl optionally substituted by 1-2 R₁₁; —COR₁₂,nitro, OR₁₃, SO₂R₁₄, NR₁₅R₁₆, N═CR₁₇R₁₈, C1-C6 alkylcarbamoyl, di-C1-C6alkylcarbamoyl, tri-C1-C6 alkylsilyl or di-C1-C6 alkylphosphono;

R₄ represents H; C1-C6 alkyl optionally substituted by 1-2 R₁₁; or—COR₁₂; or NR₃R₄ represents N═CR₂₁NR₂₂R₂₃, N═CR₂₄OR₂₅; or

that is unsubstituted or substituted by 1-2 groups independentlyselected from the group consisting of halogen, C1-C6 alkyl, C1-C6alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino,C1-C6 alkylamino, di-C1-C6 alkylamino and C1-C6 alkoxycarbonyl;

wherein R₁₁ independently represents halogen, hydroxy, C1-C6 alkoxy,halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl; or phenyl,naphthyl,

that is unsubstituted or substituted by 1-3 groups selected from thegroup consisting of halogen, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxyand nitro;

R₁₂ represents H, C1-C14 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, phenyl,phenoxy or benzyloxy;

R₁₃ represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl, benzyl orCHR₃₁C(O)OR₃₂; R₃₁ represents H, C1-C6 alkyl or C1-C6 alkoxy; R₃₂represents H, C1-C6 alkyl or benzyl;

R₁₄ represents C1-C6 alkyl or halo C1-C6 alkyl;

R₁₅ represents H, C1-C6 alkyl, formyl, C1-C6 alkylacyl, halo C1-C6alkylacyl, C1-C6 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl orbenzyloxycarbonyl; R₁₆ represents H or C1-C6 alkyl;

R₁₇ represents H, C1-C6 alkyl; or phenyl that is unsubstituted orsubstituted by 1-3 groups selected from the group consisting of halogen,C1-C6 alkyl and C1-C6 alkoxy; R₁₈ represents H or C1-C6 alkyl; orN═CR₁₇R₁₈ represents

R₂₁, R₂₄ each independently represent H or C1-C6 alkyl;

R₂₂, R₂₃ each independently represent H or C1-C6 alkyl; or NR₂₂R₂₃represents

R₂₅ represents C1-C6 alkyl;

the term “aryl” refers to phenyl or naphthyl; the term “heteroaryl”refers to

which is substituted by 0, 1, 2 or 3 groups selected from the groupconsisting of halogen, nitro, cyano, thiocyano, hydroxy, carboxy,mercapto, formyl; phenyl, benzyl, benzyloxy or phenoxy that isunsubstituted or substituted by at least one group from the groupconsisting of halogen, C1-C6 alkyl and C1-C6 alkoxy; C1-C6 alkyl, C2-C6alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl,OR″, SR″, —(C1-C6)alkyl-OR″, —(C1-C6)alkyl-SR″, COR″, COOR″, COSR″,SOR″, SO₂R″, OCOR″ or SCOR″ with or without halogen; and amino oraminocarbonyl substituted by one or two groups selected from the groupconsisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, phenyl, benzyl, benzyloxy,phenoxy, COR″, COOR″, SO₂R″ and OR″;

R′ each independently represents hydrogen, nitro, hydroxy, amino; orC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy,C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6alkylsulfonyl C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonylC1-C6 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6alkylaminocarbonyl, C1-C6 alkoxyaminocarbonyl, C1-C6 alkoxycarbonylC1-C6 alkyl, C1-C6 alkylaminocarbonyl C1-C6 alkyl, tri-C1-C6 alkylsilyl,di-C1-C6 alkylphosphono with or without fluoro, chloro or bromo;

R″ each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl,C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C6 alkyl.

Further preferably, A, B each independently represent halogen, C1-C6alkyl, halo C1-C6 alkyl or C3-C6 cycloalkyl;

C represents hydrogen, halogen, C1-C6 alkyl or halo C1-C6 alkyl;

Q represents C1-C6 alkyl, halo C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6alkenyl, C2-C6 alkynyl, halogen, cyano, amino, nitro, formyl, C1-C6alkoxy, C1-C6 alkylthio, C1-C6 alkoxycarbonyl, hydroxy C1-C6 alkyl,C1-C6 alkoxy C1-C2 alkyl, cyano C1-C2 alkyl, C1-C6 alkylamino C1-C2alkyl, benzyl, naphthyl, furyl, thienyl, thiazolyl, pyridyl,pyrimidinyl;

that is unsubstituted or substituted by C1-C6 alkyl; or phenyl that isunsubstituted or substituted by at least one group selected from thegroup consisting of C1-C6 alkyl, halo C1-C6 alkyl, halogen and C1-C6alkoxy;

R′ represents C1-C6 alkyl or halo C1-C6 alkyl.

R₁ and R₂ independently represent H, halogen, C1-C6 alkyl, halo C1-C6alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio,cyano, nitro, benzyl, phenoxy, phenylthio, naphthyl; phenyl that isunsubstituted or substituted by one or more group selected from thegroup consisting of halogen, C1-C6 alkyl, halo C1-C6 alkyl, C3-C6cycloalkyl, nitro, cyano, C1-C6 alkoxy, C1-C6 alkylthio, C2-C6alkenyloxy, amino, C1-C6 alkylamino, C1-C6 alkylcarbonylamino, C1-C6alkylphenylamino and phenoxyamino; or the group represented by theformula of —COR₅, wherein, R₅ represents C1-C6 alkyl, C1-C6 alkoxy,C1-C6 alkylthio, C2-C6 alkenoxy, phenoxy, benzyloxy, pyrrolyl C1-C2alkyloxy, C1-C6 alkylamino, C1-C6 alkylamino, C1-C6 alkylphenylamino,furyl C1-C2 alkylamino, phenylethyleneamino; or benzylamino that isunsubstituted or substituted by C1-C6 alkyl, halogen or C1-C6 alkoxy;

Or

represents

M represents amino, C1-C6 alkylamino, C1-C6 alkylcarbonylamino,phenylcarbonylamino, benzylamino; or furylmethyleneamino that isunsubstituted or substituted by halo C1-C6 alkyl.

More further preferably, A, B each independently represent fluoro,chloro, bromo, iodo, methyl, ethyl, propyl, isopropyl, trifluoromethylor cyclopropyl;

C represents hydrogen, fluoro, chloro, bromo, iodo, methyl ortrifluoromethyl;

Q represents methyl, ethyl, propyl, isopropyl, cyclopropyl, vinyl,ethynyl, fluoro, chloro, bromo, cyano, amino, nitro, formyl, methoxy,methylthio, methoxycarbonyl, monochloromethyl, monofluoromethyl,difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl,hydroxymethyl,

benzyl, naphthyl, furyl, thienyl, thiazolyl, pyridyl, pyrimidinyl;

that is unsubstituted or substituted by methyl; or phenyl that isunsubstituted or substituted by at least one group selected from thegroup consisting of methyl, trifluoromethyl, chloro and methoxy;

R′ represents methyl, ethyl or difluoromethyl;

R₁ and R₂ independently represent hydrogen, fluorine, chlorine, bromine,methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl,allyl, 2-chloroethyl, methylthio, ethylthio, ethoxy, cyano, nitro,benzyl, phenoxy, phenylthio, naphthyl; phenyl that is unsubstituted orsubstituted by one or more group selected from the group consisting offluoro, chloro, ethyl, cyclopropyl, trifluoromethyl, nitro, cyano,methoxy, methylthio, propenyloxy, amino, dimethylamino, acetamido,phenoxyamino and methylphenylamino; or the group represented by theformula of —COR₅, wherein, R₅ represents methyl, ethyl, methoxy, ethoxy,methylthio, vinyloxy, phenoxy, benzyloxy, pyrrolylmethyleneoxy,dimethylamino, propylamino, methylphenylamino, furylmethyleneamino,phenethylenylamino, or benzylamino that is unsubstituted or substitutedby methyl, chloro or methoxy;

Or

represents

M represents NH₂,

In the definition of the compound represented by the above generalformula I and in all the structural formula below, the term, whetherused alone or in a compound name, refers to the following substituent:an alkyl group having more than two carbon atoms may be straight orbranched. For example, in the compound name “-alkyl-OR″”, alkyl may be—CH₂—, —CH₂CH₂—, —CH(CH₃)—, —C(CH₃)₂— and the like. The alkyl group is,for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such asn-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl,tert-butyl or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6-alkyl-hexylsuch as n-hexyl, isohexyl or 1,3-dimethylbutyl. Similarly, alkenylincludes, for example, allyl, 1-methylprop-2-en-1-yl,2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl,1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl includes, forexample, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.Multiple bond can be at any position of each unsaturated group.Cycloalkyl is a carbocyclic saturated ring system having, for example,three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentylor cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl having,for example, three to six carbocyclic members, such as cyclopropenyl,cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bond canbe at any position. Halogen is fluorine, chlorine, bromine or iodine

If a group is substituted by a group, it is understood to mean that thegroup is substituted by one or more identical or different groupsselected from those mentioned above. Further, the same or differentsubstitution characters contained in the same or different substituentsare independently selected, and may be the same or different.

In addition, unless specifically indicated, the term occurring before orafter multiple juxtaposed substituents (separated by “,” or “or”) in thepresent invention has a limiting effect on each of the subsequentsubstituents, for example, the term “with or without halogen” in “alkylor cycloalkylalkyl with or without halogen” has a limiting effect oneach of the following groups “alkyl” and “cycloalkylalkyl”; a group(including heterocyclyl, aryl, etc.) without being specified a linkingsite may be attached at any site, including a C or N site; if it issubstituted, the substituent may be substituted at any site as long asit comply with the valence bond theory. For example, if the heteroaryl

is substituted with one methyl, it can be

etc.

Depending on the property of substituents and the linkage mannerthereof, the compound of Formula I may exist as a stereoisomer. Forexample, if a compound has one or more asymmetric carbon atoms, it mayhas enantiomers and diastereomers. The stereoisomer can be obtained fromthe mixtures obtained in the preparation by conventional separationmethods, for example by chromatographic separation. The stereoisomer mayalso be prepared selectively by using stereoselective reactions andusing optically active starting materials and/or auxiliaries. Thepresent invention also relates to all stereoisomers and mixtures thereofwhich are included in the general Formula I but are not specificallydefined.

The preparation method of the pyridyloxy carboxylic oxime derivativecomprises the following steps:

A compound of formula II is reacted with a compound of formula III toobtain a compound of formula I; the reaction scheme is as follows:

wherein, the reaction is carried out in the presence of a dehydrant anda solvent, preferably the dehydrant is DCC, and the solvent is one ormore selected from the group consisting of dichloromethane,dichloroethane, acetonitrile, N,N-dimethylformamide,N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene andxylene.

A herbicidal composition comprising (i) at least one of the pyridyloxycarboxylic oxime derivatives of the formula I; preferably, furthercomprising (ii) one or more further herbicides and/or safeners; morepreferably, further comprising (iii) agrochemically acceptableformulation auxiliaries.

A method for controlling a weed comprising applying a herbicidallyeffective amount of at least one of the pyridyloxy carboxylic oximederivatives or the herbicidal composition on a plant or in a weed area.Preferably, the plant is rice (such as japonica rice, indica rice); orthe weed is a gramineous weed (such as Digitaria sanguinalis,Echinochloa crusgalli, Setaria viridis, Leptochloa chinensis), abroad-leaved weed (such as Monochoria Vaginalis, Galium spurium,Sagittaria trifolia, Murdannia triquetra) or cyperaceae weed (such asCyperus iria, Scirpus juncoides).

Use of at least one of the pyridyloxy carboxylic oxime derivatives orthe herbicidal composition for controlling a weed, preferably, thepyridyloxy carboxylic oxime derivatives thereof being used to control aweed in a useful crop, wherein the useful crop is a genetically modifiedcrop or a crop treated by gene editing technology. Preferably, the cropis rice (such as japonica rice, indica rice); or the weed is agramineous weed (such as Digitaria sanguinalis, Echinochloa crusgalli,Setaria viridis, Leptochloa chinensis), a broad-leaved weed (such asMonochoria Vaginalis, Galium spurium, Sagittaria trifolia, Murdanniatriquetra) or cyperaceae weed (such as Cyperus iria, Scirpus juncoides).

The compounds of the formula I according to the invention have anoutstanding herbicidal activity against a broad spectrum of economicallyimportant monocotyledonous and dicotyledonous harmful plants. The activecompounds also act efficiently on perennial weeds which produce shootsfrom rhizomes, root stocks or other perennial organs and which aredifficult to control. In this context, it is generally immaterialwhether the substances are applied pre-sowing, pre-emergence orpost-emergence. Specifically, examples may be mentioned of somerepresentatives of the monocotyledonous and dicotyledonous weed florawhich can be controlled by the compounds according to the invention,without these being a restriction to certain species. Examples of weedspecies on which the active compounds act efficiently are, from amongstthe monocotyledons, Avena, Lolium, Alopecurus, Phalaris, Echinochloa,Digitaria, Setaria and also Cyperus species from the annual sector andfrom amongst the perennial species Agropyron, Cynodon, Imperata andSorghum, and also perennial Cyperus species.

In the case of the dicotyledonous weed species, the spectrum of actionextends to species such as, for example, Galium, Viola, Veronica,Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria andAbutilon from amongst the annuals, and Convolvulus, Cirsium, Rumex andArtemisia in the case of the perennial weeds. The active compoundsaccording to the invention also effect outstanding control of harmfulplants which occur under the specific conditions of rice growing suchas, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpusand Cyperus. If the compounds according to the invention are applied tothe soil surface prior to germination, then the weed seedlings areeither prevented completely from emerging, or the weeds grow until theyhave reached the cotyledon stage but then their growth stops, and,eventually, after three to four weeks have elapsed, they die completely.In particular, the compounds according to the invention exhibitexcellent activity against Apera spica venti, Chenopodium album, Lamiumpurpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia,Veronica persica, Viola tricolor and against Amaranthus, Galium andKochia species.

Although the compounds according to the invention have an excellentherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops such as, for example, wheat,barley, rye, rice, corn, sugarbeet, cotton and soya, are not damaged atall, or only to a negligible extent. In particular, they have excellentcompatibility in cereals, such as wheat, barley and corn, in particularwheat. For these reasons, the present compounds are highly suitable forselectively controlling undesired plant growth in plantings foragricultural use or in plantings of ornamentals.

Owing to their herbicidal properties, these active compounds can also beemployed for controlling harmful plants in crops of known or still to bedeveloped genetically engineered plants. The transgenic plants generallyhave particularly advantageous properties, for example resistance tocertain pesticides, in particular certain herbicides, resistance toplant diseases or causative organisms of plant diseases, such as certaininsects or microorganisms such as fungi, bacteria or viruses. Otherparticular properties relate, for example, to the quantity, quality,storage-stability, composition and to specific ingredients of theharvested product. Thus, transgenic plants having an increased starchcontent or a modified quality of the starch or those having a differentfatty acid composition of the harvested produce are known.

The use of the compounds of the formula I according to the invention ortheir salts in economically important transgenic crops of useful andornamental plants, for example of cereal, such as wheat, barley, rye,oats, millet, rice, maniok and corn, or else in crops of sugarbeet,cotton, soya, rapeseed, potato, tomato, pea and other vegetable speciesis preferred. The compounds of the formula I can preferably be used asherbicides in crops of useful plants which are resistant or which havebeen made resistant by genetic engineering toward the phytotoxic effectsof the herbicides.

Conventional ways for preparing novel plants which have modifiedproperties compared to known plants comprise, for example, traditionalbreeding methods and the generation of mutants. Alternatively, novelplants having modified properties can be generated with the aid ofgenetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0131 624). For example, there have been described several cases ofgenetically engineered changes in crop plants in order to modify thestarch synthesized in the plants (for example WO 92/11376, WO 92/14827,WO 91/19806),

transgenic crop plants which are resistant to certain herbicides of theglufosinate (Glufosinate ammonium)-(cf., for example, EP-A 0 242 236,EP-A 0 242 246) or glyphosate-type (WO 92/00377), or of thesulfonylurea-type (EP-A 0 257 993, U.S. Pat. No. 5,013,659 A),

transgenic crop plants, for example cotton, having the ability toproduce Bacillus thuringiensis toxins (Bt toxins) which impartresistance to certain pests to the plants (EP-A 0 142 924, EP-A 0 193259), transgenic crop plants having a modified fatty acid composition(WO 91/13972).

Numerous molecular biological techniques which allow the preparation ofnovel transgenic plants having modified properties are known inprinciple; see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones],VCH Weinheim, 2nd edition 1996, or Christou, “Trends in Plant Science” 1(1996) 423-431). In order to carry out such genetic engineeringmanipulations, it is possible to introduce nucleic acid molecules intoplasmids which allow a mutagenesis or a change in the sequence to occurby recombination of DNA sequences. Using the abovementioned standardprocesses it is possible, for example, to exchange bases, to removepartial sequences or to add natural or synthetic sequences. To link theDNA fragments with each other, it is possible to attach adaptors orlinkers to the fragments.

Plant cells having a reduced activity of a gene product can be prepared,for example, by expressing at least one appropriate antisense-RNA, asense-RNA to achieve a cosuppression effect, or by expressing at leastone appropriately constructed ribozyme which specifically cleavestranscripts of the abovementioned gene product.

To this end it is possible to employ both DNA molecules which comprisethe entire coding sequence of a gene product including any flankingsequences that may be present, and DNA molecules which comprise onlyparts of the coding sequence, it being necessary for these parts to belong enough to cause an antisense effect in the cells. It is alsopossible to use DNA sequences which have a high degree of homology tothe coding sequences of a gene product but which are not entirelyidentical.

When expressing nucleic acid molecules in plants, the synthesizedprotein can be localized in any desired compartment of the plant cells.However, to achieve localization in a certain compartment, it is, forexample, possible to link the coding region with DNA sequences whichensure localization in a certain compartment. Such sequences are knownto the person skilled in the art (see, for example, Braun et al., EMBOJ. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85(1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated to whole plants usingknown techniques. The transgenic plants can in principle be plants ofany desired plant species, i. e. both monocotyledonous anddicotyledonous plants. In this manner, it is possible to obtaintransgenic plants which have modified properties by overexpression,suppression or inhibition of homologous (=natural) genes or genesequences or by expression of heterologous (=foreign) genes or genesequences.

When using the active compounds according to the invention in transgeniccrops, in addition to the effects against harmful plants which can beobserved in other crops, there are frequently effects which are specificfor the application in the respective transgenic crop, for example amodified or specifically broadened spectrum of weeds which can becontrolled, modified application rates which can be used for theapplication, preferably good combinability with the herbicides to whichthe transgenic crops are resistant, and an effect on the growth and theyield of the transgenic crop plants. The invention therefore alsoprovides for the use of the compounds according to the invention asherbicides for controlling harmful plants in transgenic crop plants.

In addition, the substances according to the invention have outstandinggrowth-regulating properties in crop plants. They engage in the plantmetabolism in a regulating manner and can this be employed for thetargeted control of plant constituents and for facilitating harvesting,for example by provoking desiccation and stunted growth. Furthermore,they are also suitable for generally regulating and inhibitingundesirable vegetative growth, without destroying the plants in theprocess. Inhibition of vegetative growth plays an important role in manymonocotyledon and dicotyledon crops because lodging can be reducedhereby, or prevented completely.

The compounds according to the invention can be applied in the customaryformulations in the form of wettable powders, emulsifiable concentrates,sprayable solutions, dusts or granules. The invention therefore alsoprovides herbicidal compositions comprising compounds of the formula I.The compounds of the formula I can be formulated in various waysdepending on the prevailing biological and/or chemico-physicalparameters. Examples of suitable formulation options are: wettablepowders (WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil dispersions (OD), oil- or water-based dispersions,oil-miscible solutions, dusts (DP), capsule suspensions (CS),seed-dressing compositions, granules for broadcasting and soilapplication, granules (GR) in the form of microgranules, spray granules,coating granules and adsorption granules, water-dispersible granules(WG), water-soluble granules (SG), ULV formulations, microcapsules andwaxes. These individual formulation types are known in principle and aredescribed, for example, in Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker,N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G.Goodwin Ltd. London.

The necessary formulation auxiliaries, such as inert materials,surfactants, solvents and other additives, are likewise known and aredescribed, for example, in Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N. J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N. J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflüchenaktive Äthylenoxidaddkte” [Surface-active ethylene oxideadducts], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], Volume 7, C. HauserVerlag Munich, 4th Edition 1986.

Wettable powders are preparations which are uniformly dispersible inwater and which contain, in addition to the active compound and as wellas a diluent or inert substance, surfactants of ionic and/or nonionictype (wetting agents, dispersants), for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines,fatty alcohol polyglycol ethersulfates, alkanesulfonates,alkylbenzenesulfonates, sodium ligninsulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutyinaphthalenesulfona-te or else sodium oleoylmethyltaurinate. Toprepare the wettable powders, the herbicidally active compounds arefinely ground, for example in customary apparatus such as hammer mills,fan mills and air-jet mills, and are mixed simultaneously orsubsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromaticcompounds or hydrocarbons or mixtures of the solvents, with the additionof one or more surfactants of ionic and/or nonionic type (emulsifiers).Examples of emulsifiers which can be used are calciumalkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionicemulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycolethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxidecondensation products, alkyl polyethers, sorbitan esters, for examplesorbitan fatty acid esters or polyoxyethylene sorbitan esters, forexample polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with finely dividedsolid substances, for example talc, natural clays, such as kaolin,bentonite and pyrophyllite, or diatomaceous earth. Suspensionconcentrates can be water- or oil-based. They can be prepared, forexample, by wet milling using commercially customary bead mills, with orwithout the addition of surfactants as already mentioned above, forexample, in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared forexample by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and, if desired, surfactants as alreadymentioned above, for example, in the case of the other formulationtypes.

Granules can be prepared either by spraying the active compound ontoadsorptive, granulated inert material or by applying active-compoundconcentrates to the surface of carriers such as sand, kaolinites orgranulated inert material, by means of adhesive binders, for examplepolyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitableactive compounds can also be granulated in the manner which is customaryfor the preparation of fertilizer granules, if desired as a mixture withfertilizers. Water-dispersible granules are generally prepared by thecustomary processes, such as spray-drying, fluidized-bed granulation,disk granulation, mixing using high-speed mixers, and extrusion withoutsolid inert material.

For the preparation of disk, fluidized-bed, extruder and spray granules,see for example processes in “Spray-Drying Handbook” 3rd ed. 1979, G.Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical andEngineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”,5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details onthe formulation of crop protection products, see for example G. C.Klingman, “Weed Control as a Science”, John Wiley and Sons Inc., NewYork, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed ControlHandbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968,pages 101-103.

The agrochemical formulations generally contain from 0.1 to 99% byweight, in particular from 0.1 to 95% by weight, of active compound ofthe formula I. In wettable powders the concentration of active compoundis, for example, from about 10 to 99% by weight, the remainder to 100%by weight consisting of customary formulation constituents. Inemulsifiable concentrates the concentration of active compound can befrom about 1 to 90%, preferably from 5 to 80%, by weight. Formulationsin the form of dusts contain from 1 to 30% by weight of active compound,preferably most commonly from 5 to 20% by weight of active compound,while sprayable solutions contain from about 0.05 to 80%, preferablyfrom 2 to 50%, by weight of active compound. In the case ofwater-dispersible granules the content of active compound depends partlyon whether the active compound is in liquid or solid form and on thegranulation auxiliaries, fillers, etc. that are used. Inwater-dispersible granules the content of active compound, for example,is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, said formulations of active compound may comprise thetackifiers, wetting agents, dispersants, emulsifiers, penetrants,preservatives, antifreeze agents, solvents, fillers, carriers,colorants, antifoams, evaporation inhibitors and pH and viscosityregulators which are customary in each case.

Based on these formulations it is also possible to produce combinationswith other pesticidally active substances, for example insecticides,acaricides, herbicides and fungicides, and also with safeners,fertilizers and/or growth regulators, for example in the form of aready-mix or tank mix.

Suitable active compounds which can be combined with the activecompounds according to the invention in mixed formulations or in a tankmix are, for example, known active compounds as described in for exampleWorld Herbicide New Product Technology Handbook, China AgriculturalScience and Farming Techniques Press, 2010. 9 and in the literaturecited therein. For example the following active compounds may bementioned as herbicides which can be combined with the compounds of theformula I (note: the compounds are either named by the “common name” inaccordance with the International Organization for Standardization (ISO)or by the chemical names, if appropriate together with a customary codenumber): acetochlor, butachlor, alachlor, propisochlor, metolachlor,s-metolachlor, pretilachlor, propachlor, ethachlor, napropamide, R-lefthanded napropamide, propanil, mefenacet, diphenamid, diflufenican,ethaprochlor, beflubutamid, bromobutide, dimethenamid, dimethenamid-P,etobenzanid, flufenacet, thenylchlor, metazachlor, isoxaben,flamprop-M-methyl, flamprop-M-propyl, allidochlor, pethoxamid,chloranocryl, cyprazine, mefluidide, monalide, delachlor, prynachlor,terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor,clomeprop, propyzamide, pentanochlor, carbetamide, benzoylprop-ethyl,cyprazole, butenachlor, tebutam, benzipram, mogrton, dichlofluanid,naproanilide, diethatyl-ethyl, naptalam, flufenacet, benzadox,chlorthiamid, chlorophthalimide, isocarbamide, picolinafen, atrazine,simazine, prometryn, cyanatryn, simetryn, ametryn, propazine,dipropetryn, SSH-108, terbutryn, terbuthylazine, triaziflam, cyprazine,proglinazine, trietazine, prometon, simetone, aziprotryne, desmetryn,dimethametryn, procyazine, mesoprazine, sebuthylazine, secbumeton,terbumeton, methoprotryne, cyanatryn, ipazine, chlorazine, atraton,pendimethalin, eglinazine, cyanuric acid, indaziflam, chlorsulfuron,metsulfuron-methyl, bensulfuron methyl, chlorimuron-ethyl,tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl,mesosulfuron, iodosulfuron-methyl sodium, foramsulfuron, cinosulfuron,triasulfuron, sulfometuron methyl, nicosulfuron, ethametsulfuron-methyl,amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron,azimsulfuron, flazasulfuron, monosulfuron, monosulfuron-ester,flucarbazone-sodium, flupyrsulfuron-methyl, halosulfuron-methyl,oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone,prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron-methyl,tritosulfuron, sodium metsulfuron methyl, flucetosulfuron, HNPC-C,orthosulfamuron, propyrisulfuron, metazosulfuron, acifluorfen,fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlornitrofen,aclonifen, ethoxyfen-ethyl, bifenox, nitrofluorfen, chlomethoxyfen,fluorodifen, fluoronitrofen, furyloxyfen, nitrofen, TOPE, DMNP, PPG1013,AKH-7088, halosafen, chlortoluron, isoproturon, linuron, diuron, dymron,fluometuron, benzthiazuron, methabenzthiazuron, cumyluron, ethidimuron,isouron, tebuthiuron, buturon, chlorbromuron, methyldymron,phenobenzuron, SK-85, metobromuron, metoxuron, afesin, monuron, siduron,fenuron, fluothiuron, neburon, chloroxuron, noruron, isonoruron,3-cyclooctyl-1, thiazfluron, tebuthiuron, difenoxuron, parafluron,methylamine tribunil, karbutilate, trimeturon, dimefuron, monisouron,anisuron, methiuron, chloreturon, tetrafluron, phenmedipham,phenmedipham-ethyl, desmedipham, asulam, terbucarb, barban, propham,chlorpropham, rowmate, swep, chlorbufam, carboxazole, chlorprocarb,fenasulam, BCPC, CPPC, carbasulam, butylate, benthiocarb, vernolate,molinate, triallate, dimepiperate, esprocarb, pyributicarb, cycloate,avadex, EPTC, ethiolate, orbencarb, pebulate, prosulfocarb, tiocarbazil,CDEC, dimexano, isopolinate, methiobencarb, 2,4-D butyl ester, MCPA-Na,2,4-D isooctyl ester, MCPA isooctyl ester, 2,4-D sodium salt, 2,4-Ddimethyla mine salt, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high2,4-D propionic acid salt, 2,4-D butyric acid, MCPA propionic acid, MCPApropionic acid salt, MCPA butyric acid, 2,4,5-D, 2,4,5-D propionic acid,2,4,5-D butyric acid, MCPA amine salt, dicamba, erbon, chlorfenac,saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop-butyl,fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl,quizalofop-p-ethyl, fenoxaprop-ethy, fenoxaprop-p-ethyl, propaquizafop,cyhalofop-butyl, metamifop, clodinafop-propargyl, fenthiaprop-ethyl,chloroazifop-propynyl, poppenate-methyl, trifopsime, isoxapyrifop,paraquat, diquat, oryzalin, ethalfluralin, isopropalin, nitralin,profluralin, prodinamine, benfluralin, fluchloraline, dinitramina,dipropalin, chlornidine, methalpropalin, dinoprop, glyphosate, anilofos,glufosinate ammonium, amiprophos-methyl, sulphosate, piperophos,bialaphos-sodium, bensulide, butamifos, phocarb, 2,4-DEP, H-9201,zytron, imazapyr, imazethapyr, imazaquin, imazamox, imazamox ammoniumsalt, imazapic, imazamethabenz-methyl, fluroxypyr, fluroxypyr isooctylester, clopyralid, picloram, trichlopyr, dithiopyr, haloxydine,3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid,diflufenzopyr, triclopyr-butotyl, Cliodinate, sethoxydim, clethodim,cycloxydim, alloxydim, clefoxydim, butroxydim, tralkoxydim,tepraloxydim, buthidazole, metribuzin, hexazinone, metamitron, ethiozin,ametridione, amibuzin, bromoxynil, bromoxynil octanoate, ioxyniloctanoate, ioxynil, dichlobenil, diphenatrile, pyraclonil, chloroxynil,iodobonil, flumetsulam, florasulam, penoxsulam, metosulam,cloransulam-methyl, diclosulam, pyroxsulam, benfuresate,bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl,pyrithiobac-sodium, benzobicylon, mesotrione, sulcotrione, tembotrione,tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone,fenoxasulfone, methiozolin, fluazolate, pyraflufen-ethyl, pyrazolynate,difenzoquat, pyrazoxyfen, benzofenap, nipyraclofen, pyrasulfotole,topramezone, pyroxasulfone, cafenstrole, flupoxam, aminotriazole,amicarbazone, azafenidin, carfentrazone-ethyl, sulfentrazone,bencarbazone, benzfendizone, butafenacil, bromacil, isocil, lenacil,terbacil, flupropacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin,propyzamide, MK-129, flumezin, pentachlorophenol, dinoseb, dinoterb,dinoterb acetate, dinosam, DNOC, chloronitrophene, medinoterb acetate,dinofenate, oxadiargyl, oxadiazon, pentoxazone, Flufenacet,fluthiacet-methyl, fentrazamide, flufenpyr-ethyl, pyrazon, brompyrazon,metflurazon, kusakira, dimidazon, oxapyrazon, norflurazon, pyridafol,quinclorac, quinmerac, bentazone, pyridate, oxaziclomefone, benazolin,clomazone, cinmethylin, ZJ0702, pyribambenz-propyl, indanofan, sodiumchlorate, dalapon, trichloroacetic acid, monochloroacetic acid,hexachloroacetone, flupropanate, cyperquat, bromofenoxim, epronaz,methazole, flurtamone, benfuresate, ethofumesate, tioclorim, chlorthal,fluorochloridone, tavron, acrolein, bentranil, tridiphane,chlorfenpropmethyl, thidiarizonaimin, phenisopham, busoxinone,methoxyphenone, saflufenacil, clacyfos, chloropon, alorac, diethamquat,etnipromid, iprymidam, ipfencarbazone, thiencarbazone-methyl,pyrimisulfan, chlorflurazole, tripropindan, sulglycapin, prosulfalin,cambendichlor, aminocyclopyrachlor, rodethanil, benoxacor, fenclorim,flurazole, fenchlorazole-ethyl, cloquintocet-mexyl, oxabetrinil, MG/91,cyometrinil, DKA-24, mefenpyr-diethyl, furilazole, fluxofenim,isoxadifen-ethyl, dichlormid, halauxifen-methyl, DOW florpyrauxifen,UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189,SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751,KIH-6127 and KIH-2023.

In the context of the present specification, if an abbreviation of ageneric name of an active compound is used, it includes in each case allcustomary derivatives, such as esters and salts, as well as isomers, inparticular optical isomers, especially one or more commerciallyavailable forms. If the generic name denotes an ester or a salt, it alsoincludes in each case all other conventional derivatives, such as otheresters and salts, free acids and neutral compounds, as well as isomers,in particular optical isomers, especially one or more commerciallyavailable forms. The chemical name given to a compound means at leastone compound encompassed by the generic name, and generally thepreferred compound.

For use, the formulations which are present in commercially availableform are, if appropriate, diluted in the customary manner, for exampleusing water in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules. Products in the form ofdusts, granules for soil application or broadcasting and sprayablesolutions are usually not further diluted with other inert substancesprior to use. The application rate of the compounds of the formula Irequired varies with the external conditions, such as temperature,humidity, the nature of the herbicide used and the like. It can varywithin wide limits, for example between 0.001 and 1.0 kg a.i./ha or moreof active substance, but it is preferably between 0.005 and 750 ga.i./ha, in particular between 0.005 and 500 g a.i./ha.

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

The following examples are intended to illustrate the present inventionand should not be construed as limiting the present invention in anyway. The scope for which protection is sought in the present inventionis intended to be defined by the claims.

In view of economics and variety of a compound, we preferablysynthesized several compounds, part of which are listed in the followingTable 1. The structure and information of a certain compound are shownin Tables 1-2. The compounds in Table 1 are listed for furtherexplication of the present invention, other than any limit therefor. Thesubject of the present invention should not be interpreted by thoseskilled in the art as being limited to the following compounds.

TABLE 1 The structure of compounds

No. A B C Q R₁ R₂ M 1 F F F CH₃ Me Me NH₂ 2 Cl Cl Cl CH₃ Me Ph NH₂ 3 ClCl H CH₃ Ph Ph NH₂ 4 Cl Cl F CH₃ Me Ph NH₂ 5 Cl Cl CH₃ CH₃ Me Ph NH₂ 6Cl Cl CF₃ CH₃ Me Ph NH₂ 7 CH₃ CH₃ F CH₃ Me Ph NH₂ 8 Et Et CF₃ CH₃ Me PhNH₂ 9

Cl H CH₃ Ph Ph NH₂ 10

Cl Cl CH₃ Me Ph NH₂ 11 F

CF₃ CH₃ Me Ph NH₂ 12 Br Br F CH₃ Me Ph NH₂ 13 I I H CH₃ Ph Ph NH₂ 14

F CH₃ Me Ph NH₂ 15 CF₃ Cl F CH₃ Me Me NH₂ 16 Cl CF₃ H CH₃ Me Me NH₂ 17Cl Cl I CH₃ Me —CH(CH₃)₂ NH₂ 18 Cl

Br CH₃ Ph Ph NH₂ 19 CH₃ CH₃ CH₃ CH₃ Me CH₂CH₂Cl NH₂ 20 Cl CH₃ F CH₃ MeMe NH₂ 21 Cl CH₃ H CH₃ Me Me NH₂ 22 Cl

F CH₃ Me Me NH₂ 23 Cl Cl H CH₃ Me Me NH₂ 24 Cl Cl Cl CH₃ Me Me NH₂ 25 ClCl F Et Me Ph NH₂ 26 Cl Cl F

Me Ph NH₂ 27 Cl Cl F

Me Et NH₂ 28 Cl Cl F

Me —CH₂CH₂CH₃ NH₂ 29 Cl Cl F

Me Ph NH₂ 30 Cl Cl F

Me Ph NH₂ 31 Cl Cl F

Me —C(CH₃)₃ NH₂ 32 Cl Cl F

Me Me NH₂ 33 Cl Cl F

Me Me NH₂ 34 Cl Cl F F Me Me NH₂ 35 Cl Cl F Cl Me Me NH₂ 36 Cl Cl F BrMe Me NH₂ 37 Cl Cl F

Me Me NH₂ 38 Cl Cl F

Me Me NH₂ 39 Cl Cl F

Me Me NH₂ 40 Cl Cl F

Me Me NH₂ 41 Cl Cl F CF₃ Me Me NH₂ 42 Cl Cl F

Me Me NH₂ 43 Cl Cl F CN Me Me NH₂ 44 Cl Cl F

Me Me NH₂ 45 Cl Cl F NH₂ Me Me NH₂ 46 Cl Cl F

Me Me NH₂ 47 Cl Cl F

Me Me NH₂ 48 Cl Cl F

Me Me NH₂ 49 Cl Cl F NO₂ Me Me NH₂ 50 Cl Cl F

Me Me NH₂ 51 Cl Cl F

Me Me NH₂ 52 Cl Cl F

Me Me NH₂ 53 Cl Cl F

Me Me NH₂ 54 Cl Cl F

Me Me NH₂ 55 Cl Cl F

Me Me NH₂ 56 Cl Cl F

Me Me NH₂ 57 Cl Cl F

Me Me NH₂ 58 Cl Cl F

Me Me NH₂ 59 Cl Cl F

Me Me NH₂ 60 Cl Cl F

Me Ph NH₂ 61 Cl Cl F

Me OEt NH₂ 62 Cl Cl F

H H NH₂ 63 Cl Cl F

H Et NH₂ 64 Cl Cl F

Me Me NH₂ 65 Cl Cl F

Me Me NH₂ 66 Cl Cl F

Et Et NH₂ 67 Cl Cl F CH₃ Me Me NH₂ 68 Cl Cl F CH₃ Et —CH(CH₃)₂ NH₂ 69 ClCl F CH₃ Et n-Bu NH₂ 70 Cl Cl F CH₃ Me 4-Cl, Ph NH₂ 71 Cl Cl F CH₃ Me4-NO₂, Ph NH₂ 72 Cl Cl F CH₃ H Ph NH₂ 73 Cl Cl F CH₃ H 3-NO₂, Ph NH₂ 74Cl Cl F CH₃ Et Ph NH₂ 75 Cl Cl F CH₃ CH₂CH₂CH₃ Cl NH₂ 76 Cl Cl F CH₃n-Bu OEt NH₂ 77 Cl Cl F CH₃ Ph

NH₂ 78 Cl Cl F CH₃ Ph Ph NH₂ 79 Cl Cl F CH₃ Ph 3-Cl, Ph NH₂ 80 Cl Cl FCH₃ Ph

NH₂ 81 Cl Cl F CH₃ 4-CF₃, Ph Ph NH₂ 82 Cl Cl F CH₃ 3-F, Ph 4-Cl, Ph NH₂83 Cl Cl F CH₃ 4-F, Ph Ph NH₂ 84 Cl Cl F CH₃ F 2-OMe, Ph NH₂ 85 Cl Cl FCH₃ Cl 3-Et, Ph NH₂ 86 Cl Cl F CH₃ Br 4-CN, Ph NH₂ 87 Cl Cl F CH₃ CN4-Cl, Ph NH₂ 88 Cl Cl F CH₃ OEt 4-NHCOMe, Ph NH₂ 89 Cl Cl F CH₃ SMe4-SMe, Ph NH₂ 90 Cl Cl F CH₃ NO₂ 4-N(Me)₂, Ph NH₂ 91 Cl Cl F CH₃ Ac4-NHOPh, Ph NH₂ 92 Cl Cl F CH₃ COOEt

NH₂ 93 Cl Cl F CH₃ Bn 2-NH₂, Ph NH₂ 94 Cl Cl F CH₃

CONHBn NH₂ 95 Cl Cl F CH₃

NH₂ 96 Cl Cl F CH₃ OPh COOPh NH₂ 97 Cl Cl F CH₃ SPh COEt NH₂ 98 Cl Cl FCH₃ CONHPr Ph NH₂ 99 Cl Cl F CH₃ CON(Me)₂ Ph NH₂ 100 Cl Cl F CH₃

Et NH₂ 101 Cl Cl F CH₃

Ph NH₂ 102 Cl Cl F CH₃

COSMe NH₂ 103 Cl Cl F CH₃

Me NH₂ 104 Cl Cl F CH₃

Ph NH₂ 105 Cl Cl F CH₃

Ph NH₂ 106 Cl Cl F CH₃

CONMePh NH₂ 107 Cl Cl F CH₃

Ph NH₂ 108 Cl Cl F CH₃

Et NH₂ 109 Cl Cl F CH₃

COOMe NH₂ 110 Cl Cl F CH₃ CH₃ CH₃

111 Cl Cl F CH₃ CH₃ CH₃

112 Cl Cl F CH₃ CH₃ CH₃

113 Cl Cl F CH₃ CH₃ CH₃

114 Cl Cl F CH₃ CH₃ CH₃

115 Cl Cl F CH₃ CH₃ CH₃

116 Cl Cl F CH₃

represents

NH₂ 117 Cl Cl F CH₃

represents

NH₂ 118 Cl Cl F CH₃ CH₃ CH₃

TABLE 2 ¹H NMR data of compounds No. ¹H NMR 1 ¹H NMR (500 MHz, DMSO-d₆)δ 6.36 (s, 2H), 4.49 (q, J = 7.0 Hz, 1H), 2.45 (s, 3H), 2.42 (s, 3H),1.60 (d, J = 7.0 Hz, 3H). 2 ¹H NMR (500 MHz, DMSO-d₆) δ 7.59-7.46 (m,5H), 6.78 (s, 2H), 4.75 (q, J = 7.0 Hz, 1H), 2.74 (s, 3H), 1.57 (d, J =7.0 Hz, 3H). 3 ¹H NMR (500 MHz, DMSO-d₆) δ 7.65 (s, 1H), 7.54-7.50 (m,2H), 7.45-7.34 (m, 8H), 6.83 (s, 2H), 4.65 (q, J = 7.0 Hz, 1H), 1.49 (d,J = 7.0 Hz, 3H). 4 ¹H NMR (500 MHz, DMSO-d₆) δ 7.59-7.49 (m, 3H), 7.48(dd, J = 7.5, 2.0 Hz, 2H), 6.78 (s, 2H), 4.71 (q, J = 7.0 Hz, 1H), 2.72(s, 3H), 1.58 (d, J = 7.0 Hz, 3H). 5 ¹H NMR (500 MHz, DMSO-d₆) δ7.59-7.46 (m, 5H), 6.71 (s, 2H), 4.71 (q, J = 7.0 Hz, 1H), 2.79 (s, 3H),2.53 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H). 6 ¹H NMR (500 MHz, DMSO-d₆) δ7.59-7.48 (m, 5H), 6.82 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 2.87 (s, 3H),1.48 (d, J = 7.0 Hz, 3H). 7 ¹H NMR (500 MHz, DMSO-d₆) δ 7.55-7.46 (m,5H), 6.36 (s, 2H), 4.48 (q, J = 7.0 Hz, 1H), 2.79 (s, 3H), 2.14 (s, 3H),2.01 (s, 3H), 1.56 (d, J = 7.0 Hz, 3H). 8 ¹H NMR (500 MHz, DMSO-d₆) δ7.59-7.46 (m, 5H), 6.36 (s, 2H), 4.76 (q, J = 7.0 Hz, 1H), 2.74 (s, 3H),2.71-2.68 (m, 1H), 2.55-2.49 (m, 1H), 2.16-2.05 (m, 1H), 2.00-1.94 (m,1H), 1.59 (d, J = 7.0 Hz, 3H), 1.13-1.10 (m, 6H). 9 ¹H NMR (500 MHz,DMSO-d₆) δ 7.58-7.48 (m, 11H), 6.36 (s, 2H), 4.70 (q, J = 7.0 Hz, 1H),2.90-2.85 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H), 1.19-1.12 (m, 6H). 10 ¹HNMR (500 MHz, DMSO-d₆) δ 7.59-7.48 (m, 5H), 6.36 (s, 2H), 4.72 (q, J =7.0 Hz, 1H), 2.89 (s, 3H), 2.08-2.03 (m, 1H), 1.47 (d, J = 6.5 Hz, 3H),0.99-0.90 (m, 2H), 0.78-0.68 (m, 2H). 11 ¹H NMR (500 MHz, DMSO-d₆) δ7.59-7.47 (m, 5H), 6.36 (s, 2H), 4.71 (q, J = 7.0Hz, 1H), 3.22-3.17 (m,1H), 2.86 (s, 3H), 1.50 (d, J = 7.0 Hz, 3H), 1.13-1.06 (m, 6H). 12 ¹HNMR (500 MHz, DMSO-d₆) δ 7.59-7.48 (m, 5H), 6.62 (s, 2H), 4.69 (q, J =7.0 Hz, 1H), 2.87 (s, 3H), 1.48 (d, J = 7.0 Hz, 3H). 13 ¹H NMR (500 MHz,DMSO-d₆) δ 8.02 (s, 1H), 7.54-7.36 (m, 10H), 6.36 (s, 2H), 4.06 (q, J =7.0 Hz, 1H), 1.34 (d, J = 7.0 Hz, 3H). 14 ¹H NMR 500 MHz, DMSO-d₆) δ7.59-7.48 (m, 5H), 6.36 (s, 2H), 4.71 (q, J = 7.0 Hz, 1H), 2.80 (s, 3H),2.62 (t, J = 8.0 Hz, 2H), 2.02-1.98 (m, 1H), 1.64 (q, J = 8.0Hz, 2H),1.48 (d, J = 7.0 Hz, 3H), 1.07-1.00 (m, 2H), 0.94 (t, J = 8.0 Hz, 3H),0.78-0.71 (m, 2H). 15 ¹H NMR (500 MHz, DMSO-d₆) δ 6.36 (s, 2H), 4.57 (q,J = 7.0 Hz, 1H), 2.48 (s, 3H), 2.45 (s, 3H), 1.54 (d, J = 7.0 Hz, 3H).16 ¹H NMR (500 MHz, DMSO-d₆) δ 7.72 (s, 1H), 6.36 (s, 2H), 4.64 (q, J =7.0 Hz, 1H), 2.35 (s, 3H), 2.30 (s, 3H), 1.47 (d, J = 7.0 Hz, 3H). 17 ¹HNMR (500 MHz, DMSO-d₆) δ 6.53 (s, 2H), 4.60 (q, J = 7.0 Hz, 1H), 2.42(s, 3H), 1.76-1.72 (m, 1H), 1.50 (d, J = 7.0 Hz, 3H), 0.99-0.92 (m, 6H).18 ¹H NMR (500 MHz, DMSO-d₆)δ 7.54-7.50 (m, 2H), 7.48-7.40 (m, 2H),7.44-7.34 (m, 6H), 6.36 (s, 2H), 4.65 (q, J = 7.0 Hz, 1H), 2.28-2.23 (m,1H), 1.83-1.78 (m, 1H), 1.63-1.56 (m, 1H), 1.53 (d, J = 7.0 Hz, 3H),1.53-1.40 (m, 1H), 0.94 (t, J = 8.0 Hz, 3H). 19 ¹H NMR (500 MHz,DMSO-d₆) δ 6.36 (s, 2H), 4.46 (q, J = 7.0 Hz, 1H), 3.35-3.29 (m, 1H),3.22-3.16 (m, 1H), 2.84-2.78 (m, 1H), 2.53 (s, 3H), 2.40 (s, 3H),2.17-2.11 (m, 4H), 2.03 (s, 3H), 1.59 (d, J = 7.0 Hz, 3H). 20 ¹H NMR(500 MHz, DMSO-d₆) δ 6.36 (s, 2H), 4.47 (q, J = 7.0 Hz, 1H), 2.48 (s,3H), 2.44 (s, 3H), 2.07 (s, 3H), 1.40 (d, J = 7.0 Hz, 3H). 21 ¹H NMR(500 MHz, DMSO-d₆) δ 7.49 (s, 1H), 6.36 (s, 2H), 4.46 (q, J = 7.0 Hz,1H), 2.45 (s, 3H), 2.43 (s, 3H), 2.07 (s, 3H), 1.60 (d, J = 7.0 Hz, 3H).22 ¹H NMR (500 MHz, DMSO-d₆) δ 6.36 (s, 2H), 4.49 (q, J = 7.0 Hz, 1H),2.45 (s, 3H), 2.43 (s, 3H), 2.02 (p, J = 7.0 Hz, 1H), 1.45 (d, J = 7.0Hz, 3H), 0.96-0.93 (m, 2H), 0.74-0.65 (m, 2H). 23 ¹H NMR (500 MHz,DMSO-d₆) δ 7.60 (s, 1H), 6.79 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 2.43(s, 3H), 2.41 (s, 3H), 1.52 (d, J = 7.0 Hz, 3H). 24 ¹H NMR (500 MHz,DMSO-d₆) δ 6.81 (s, 2H), 4.74 (q, J = 7.0 Hz, 1H), 2.42 (s, 3H), 2.39(s, 3H), 1.47 (d, J = 7.0 Hz, 3H). 25 ¹H NMR (500 MHz, DMSO-d₆) δ7.59-7.49 (m, 3H), 7.49-7.42 (m, 2H), 6.77 (s, 2H), 4.29 (dd, J = 11.0,1.0 Hz, 1H), 2.88 (s, 3H), 2.08-1.99 (m, 1H), 1.61-1.47 (m, 1H), 0.83(t, J = 8.0 Hz, 3H). 26 ¹H NMR (500 MHz, DMSO-d₆) δ 7.59-7.48 (m, 5H),6.77 (s, 2H), 4.33 (dd, J = 11.0, 1.0 Hz, 1H), 2.89 (s, 3H), 1.90-1.79(m, 1H), 1.66-1.53 (m, 1H), 1.54-1.40 (m, 2H), 0.81 (t, J = 8.0 Hz, 3H).27 ¹H NMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 4.37 (d, J = 7.0 Hz, 1H),2.82-2.75 (m, 1H), 2.44 (s, 3H), 2.41-2.33 (m, 1H), 1.86-1.82 (m, 1H),0.95-0.88 (m, 6H), 0.86 (d, J = 7.0Hz, 3H). 28 ¹H NMR (500 MHz, DMSO-d₆)δ 6.77 (s, 2H), 3.48 (d, J = 7.0 Hz, 1H), 2.56-2.50 (m, 1H), 2.40 (s,3H), 1.97-1.86 (m, 1H), 1.11-1.06 (m, 1H), 1.10-0.96 (m, 1H), 0.92-0.85(m, 4H), 0.48-0.43 (m, 2H), 0.32-0.27 (m, 2H). 29 ¹H NMR (500 MHz,DMSO-d₆) δ 7.54-7.50 (m, 2H), 7.47-7.33 (m, 8H), 6.82 (s, 2H), 4.26 (dd,J = 11.0, 1.5 Hz, 1H), 3.55-3.49 (m, 1H), 3.20-3.15 (m, 5H), 1.31-1.26(m, 1H), 0.80-0.72 (m, 1H). 30 ¹H NMR (500 MHz, DMSO-d₆) δ 7.57-7.51 (m,3H), 7.47 (dd, J = 7.5, 2.5 Hz, 2H), 6.79 (s, 2H), 4.41 (t, J = 7.0 Hz,1H), 4.18 (dd, J = 12.5, 7.0 Hz, 1H), 3.83 (dd, J = 12.5, 7.0 Hz, 1H),3.29 (s, 3H), 2.72 (s, 3H). 31 ¹H NMR (500 MHz, DMSO-d₆) δ 6.79 (s, 2H),4.36 (d, J = 7.0 Hz, 1H), 3.89 (p, J = 7.0 Hz, 1H), 3.20 (s, 3H), 2.57(s, 3H), 1.15 (d, J = 7.0 Hz, 3H), 1.06 (s, 9H). 32 ¹H NMR (500 MHz,DMSO-d₆) δ 6.81 (s, 2H), 6.38-6.32 (m, 1H), 5.37-5.21 (m, 1H), 5.19 (dd,J = 6.0, 1.0 Hz, 1H), 5.19 (dd, J = 6.0, 1.0 Hz, 1H), 2.41 (s, 3H), 2.38(s, 3H). 33 ¹H NMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 5.69 (d, J = 3.5Hz, 1H), 3.68 (d, J = 3.0 Hz, 1H), 2.53 (s, 3H), 2.51 (s, 3H) 34 ¹H NMR(500 MHz, DMSO-d₆) δ 7.01 (d, J = 46.5 Hz, 1H), 6.81 (s, 2H), 2.45 (s,3H), 2.43 (s, 3H) 35 ¹H NMR (500 MHz, DMSO-d₆) δ 6.81 (s, 2H), 6.65 (s,1H), 2.45 (s, 3H), 2.43 (s, 3H). 36 ¹H NMR (500 MHz, DMSO-d₆) δ 6.84 (s,2H), 6.78 (s, 1H), 2.45 (s, 3H), 2.43 (s, 3H). 37 ¹H NMR (500 MHz,DMSO-d₆) δ 6.81 (s, 2H), 4.58 (t, J = 7.0 Hz, 1H), 4.33 (dd, J = 12.5,7.0 Hz, 1H), 4.09 (dd, J = 12.5, 7.0 Hz, 1H), 2.45 (s, 3H), 2.42 (s,3H). 38 ¹H NMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 5.28-4.93 (m, 2H),4.72-4.64 (m, 1H), 2.45 (s, 3H), 2.43 (s, 3H) 39 ¹H NMR (500 MHz,DMSO-d₆) δ 6.78 (s, 2H), 6.26-6.02 (m, 1H), 5.18-5.08 (m, 1H), 2.45 (s,3H), 2.43 (s, 3H). 40 ¹H NMR (500 MHz, DMSO-d₆) δ 6.85 (s, 2H), 4.24 (d,J = 9.5 Hz, 1H), 3.93-3.87 (m, 1H), 3.72-3.66 (m, 1H), 2.43-2.37 (m,7H), 1.96-1.91 (m, 1H). 41 ¹H NMR (500 MHz, DMSO-d₆) δ 6.83 (s, 2H),5.51 (q, J = 9.0 Hz, 1H), 2.45 (s, 3H), 2.42 (s, 3H). 42 ¹H NMR (500MHz, DMSO-d₆) δ 6.80 (s, 2H), 4.58-4.52 (m, 1H), 3.21-3.13 (m, 1H), 2.43(s, 3H), 2.40 (s, 3H), 2.11-2.03 (m, 1H). 43 ¹H NMR (500 MHz, DMSO-d₆) δ6.82 (s, 2H), 5.83 (s, 1H), 2.44 (s, 3H), 2.41 (s, 3H). 44 ¹H NMR (500MHz, DMSO-d₆) δ 6.81 (s, 2H), 4.87 (t, J = 7.0 Hz, 1H), 3.45 (dd, J =12.5, 7.0 Hz, 1H), 2.83 (dd, J = 12.5, 7.0 Hz, 1H), 2.44 (s, 3H), 2.40(s, 3H). 45 ¹H NMR (500 MHz, DMSO-d₆) δ 6.82 (s, 2H), 5.87 (s, 1H), 2.43(s, 3H), 2.39 (s,3H). 2.33 (s, 2H). 46 ¹H NMR (500 MHz, DMSO-d₆) δ 6.85(s, 2H), 4.52 (t, J = 7.0 Hz, 1H), 3.04 (dd, J = 12.5, 7.0 Hz, 1H), 2.71(dd, J = 12.5, 7.0 Hz, 1H), 2.45 (s, 3H), 2.43 (s, 3H), 2.17 (s, 6H). 47¹H NMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 5.76 (s, 1H), 2.49 (s, 3H),2.47 (s, 3H). 2.17 (s, 3H). 48 ¹H NMR (500 MHz, DMSO-d₆) δ 6.81 (s, 2H),4.97 (t, J = 5.5 Hz, 1H), 4.44-4.39 (m, 1H), 4.18 (t, J = 7.0 Hz, 1H),3.85-3.80 (m, 1H), 2.45 (s, 3H), 2.43 (s, 3H). 49 ¹H NMR (500 MHz,DMSO-d₆) δ 7.28 (s, 1H), 6.80 (s, 2H), 2.45 (s, 3H), 2.43 (s, 3H).. 50¹H NMR (500 MHz, DMSO-d₆) δ 6.81 (s, 2H), 6.08 (s, 1H), 3.26 (s, 3H),2.48 (s, 3H), 2.46 (s, 3H). 51 ¹H NMR (500 MHz, DMSO-d₆) δ 10.11 (d, J =6.0 Hz, 1H), 6.79 (s, 2H), 5.41 (d, J = 6.0 Hz, 1H), 2.45 (s, 3H), 2.43(s, 3H). 52 ¹H NMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 5.61 (s, 1H), 3.65(s, 3H), 2.48 (s, 3H), 2.46 (s, 3H). 53 ¹H NMR (500 MHz, DMSO-d₆) δ7.32-7.30 (m, 2H), 7.28-7.15 (m, 3H), 6.77 (s, 2H), 4.81 (t, J = 7.0 Hz,1H), 3.24-3.15 (m, 1H), 2.98-2.89 (m, 1H), 2.35 (s, 3H), 2.32 (s, 3H).54 ¹H NMR (500 MHz, DMSO-d₆) δ 7.40 (dd, J = 7.5, 2.0 Hz, 1H), 7.19 (dd,J = 7.5, 1.5 Hz, 1H), 7.05 (t, J = 7.5 Hz, 1H), 6.80 (s, 2H), 6.24 (s,1H), 2.53 (s, 3H), 2.50 (s, 3H).. 55 ¹H NMR (500 MHz, DMSO-d₆) δ 7.47(d, J = 7.5 Hz, 1H), 7.41 (d, J = 1.5 Hz, 1H), 6.81 (s, 2H), 6.37 (dd, J= 7.5, 1.5 Hz, 1H), 6.07 (s, 1H), 2.51 (s, 3H), 2.50 (s, 3H). 56 ¹H NMR(500 MHz, DMSO-d₆) δ 8.86 (s, 1H), 7.42-7.40 (m, 1H), 6.81 (s, 2H), 6.07(s, 1H), 2.52 (s, 3H), 2.50 (s, 3H). 57 ¹H NMR (500 MHz, DMSO-d₆) δ 7.58(d, J = 7.5 Hz, 1H), 6.80 (s, 2H), 6.52 (d, J = 7.5 Hz, 1H), 5.98 (s,1H), 4.70-4.62 (m, 1H), 4.26-4.19 (m, 1H), 2.53 (s, 3H), 2.51 (s, 3H),1.26 (t, J = 8.0 Hz, 3H). 58 ¹H NMR (500 MHz, DMSO-d₆) δ 7.11 (s, 1H),6.81 (s, 2H), 6.08 (s, 1H), 3.72 (s, 3H), 2.49 (s, 3H), 2.46 (s, 3H),2.33 (s, 3H). 59 ¹H NMR (500 MHz, DMSO-d₆) δ 7.83 (t, J = 57.5 Hz, 1H),7.34 (d, J = 7.5 Hz, 1H), 6.80 (s, 2H), 6.52 (d, J = 7.5 Hz, 1H), 6.28(s, 1H), 2.51 (s, 3H), 2.49 (s, 3H) 60 ¹H NMR (500 MHz, DMSO-d₆) δ7.74-7.67 (m, 2H), 7.59-7.39 (m, 8H), 6.81 (s, 2H), 5.93 (d, J = 1.5 Hz,1H), 2.85 (s, 3H). 61 ¹H NMR (500 MHz, DMSO-d₆) δ 7.79-7.77 (m, 2H),7.44-7.41 (m, 2H), 7.37-7.29 (m, 1H), 6.75 (s, 2H), 5.86 (d, J = 1.0 Hz,1H), 4.01-3.83 (m, 2H), 2.10 (s, 3H), 1.36 (t, J = 8.0 Hz, 3H). 62 ¹HNMR (500 MHz, DMSO-d₆) δ 7.99-7.94 (m, 1H), 7.59-7.57 (m, 1H), 7.43-7.32(m, 2H), 6.84 (s, 2H), 5.98 (d, J = 2.0 Hz, 1H), 5.90 (d, J = 2.0 Hz,1H), 5.82 (d, J = 1.0 Hz, 1H). 63 ¹H NMR (500 MHz, DMSO-d₆) δ 7.43 (dd,J = 7.5, 1.0 Hz, 1H), 6.92 (dd, J = 7.5, 2.0 Hz, 1H), 6.77 (s, 2H),6.74-6.69 (m, 1H), 6.30 (dd, J = 10.0, 3.5 Hz, 1H), 5.82 (d, J = 1.0 Hz,1H), 3.72 (s, 3H), 2.46-2.36 (m, 1H), 2.13 (d, J = 1.0 Hz, 3H),1.91-1.83 (m, 1H), 0.96 (t, J = 8.0 Hz, 3H). 64 ¹H NMR (500 MHz,DMSO-d₆) δ 8.71 (d, J = 1.0 Hz, 1H), 8.40 (dd, J = 5.0, 1.0 Hz, 1H),7.73 (dt, J = 8.0, 1.0 Hz, 1H), 7.51 (dd, J = 8.0, 5.0 Hz, 1H), 6.77 (s,2H), 5.91 (s, 1H), 2.43 (s, 3H), 2.41 (s, 3H). 65 ¹H NMR (500 MHz,DMSO-d₆) δ 9.12 (s, 1H), 8.83 (s, 2H), 6.77 (s, 2H), 5.78 (s, 1H), 2.45(s, 3H), 2.43 (s, 3H). 66 ¹H NMR (500 MHz, DMSO-d₆) δ 8.14 (s, 1H),8.06-8.04 (m, 1H), 8.02-7.91 (m, 2H), 7.81 (dd, J = 7.0, 1.5 Hz, 1H),7.58-7.55 (m, 2H), 6.18 (s, 2H), 6.10 (s, 1H), 2.65-2.63 (m, 2H),2.33-2.31 (m, 2H), 0.96-0.98 (m, 6H). 67 ¹H NMR (500 MHz, DMSO-d₆) δ6.79 (s, 2H), 4.73 (q, J = 7.0 Hz, 1H), 2.47 (s, 3H), 2.41 (s, 3H), 1.50(d, J = 7.0 Hz, 3H). 68 ¹H NMR (500 MHz, DMSO-d₆) δ 6.81 (s, 2H), 4.70(q, J = 7.0 Hz, 1H), 2.87-2.85 (m, 1H), 2.00-1.84 (m, 2H), 1.47 (d, J =7.0 Hz, 3H), 0.96 (d, J = 7.0 Hz, 3H), 0.91 (d, J = 7.0 Hz, 3H), 0.86(d, J = 7.0 Hz, 3H). 69 ¹H NMR (500 MHz, DMSO-d₆) δ 6.81 (s, 2H), 4.69(q, J = 7.0 Hz, 1H), 3.17-3.12 (m, 1H), 2.58-2.51 (m, 1H), 2.03-1.96 (m,1H), 1.76-1.71 (m, 1H), 1.50 (d, J = 7.0 Hz, 3H), 1.46-1.38 (m, 1H),1.27-1.06 (m, 2H), 0.94-0.88 (m, 6H), 0.77-0.64 (m, 1H). 70 ¹H NMR (500MHz, DMSO-d₆) δ 7.65-7.59 (m, 2H), 7.46-6.80 (s, 2H), 4.63 (q, J = 7.0Hz, 1H), 2.72 (s, 3H), 1.36 (d, J = 7.0 Hz, 3H). 71 ¹H NMR (500 MHz,DMSO-d₆) δ 8.35-8.28 (m, 2H), 7.65-6.79 (s, 2H), 4.70 (q, J = 7.0 Hz,1H), 2.76 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H). 72 ¹H NMR (500 MHz,DMSO-d₆) δ 7.83 (s, 1H), 7.69-7.62 (m, 2H), 7.59-7.56 (m, 1H), 7.44-7.42(m, 2H), 6.78 (s, 2H), 4.70 (q, J = 7.0 Hz, 1H), 1.45 (d, J = 7.0 Hz,3H). 73 ¹H NMR (500 MHz, DMSO-d₆) δ 8.36-8.30 (m, 2H), 7.75-7.66 (m, 3H)6.81 (s, 2H), 4.69 (q, J = 6.9 Hz, 1H), 1.43 (d, J = 7.0 Hz, 3H). 74 ¹HNMR (500 MHz, DMSO-d₆) δ 7.56-7.49 (m, 5H), 6.79 (s, 2H), 4.64 (q, J =7.0 Hz, 1H), 2.61-2.54 (m, 1H), 2.30-2.22 (m, 1H), 1.45 (d, J = 7.0 Hz,3H), 1.01 (t, J = 8.0 Hz, 3H). 75 ¹H NMR (500 MHz, DMSO-d₆) δ 6.83 (s,2H), 4.69 (q, J = 7.0 Hz, 1H), 2.74-2.71 (m, 1H), 2.36-2.34 (m, 1H),1.43 (d, J = 7.0 Hz, 3H), 1.31-1.22 (m, 1H), 0.87 (t, J = 8.0 Hz, 3H),0.49-0.39 (m, 1H). 76 ¹H NMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 4.76 (q,J = 7.0 Hz, 1H), 4.02-3.90 (m, 2H), 2.90-2.84 (m, 1H), 2.33-2.28 (m,1H), 1.74-1.64 (m, 1H), 1.45 (d, J = 6.5 Hz, 3H), 1.45-1.24 (m, 5H),1.03-0.93 (m, 1H), 0.93 (t, J = 8.0 Hz, 3H). 77 ¹H NMR (500 MHz,DMSO-d₆) δ 7.59-7.49 (m, 5H), 6.77 (s, 2H), 5.99-5.91 (m, 1H), 5.18-5.14(m, 1H), 5.10-5.00 (m, 1H), 4.61 (q, J = 7.0 Hz, 1H), 3.17-3.09 (m, 1H),2.90-2.82 (m, 1H), 1.48 (d, J = 7.0 Hz, 3H). 78 ¹H NMR (500 MHz,DMSO-d₆) δ 7.56-7.47 (m, 2H), 7.47-7.39 (m, 6H), 7.37 (t, J = 7.5 Hz,2H), 6.80 (s, 2H), 4.72 (q, J = 7.0 Hz, 1H), 1.38 (d, J = 7.0 Hz, 3H).79 ¹H NMR(500 MHz, DMSO-d₆) δ 7.72 (t, J = 2.0 Hz, 1H), 7.58-7.47 (m,2H), 7.43 (t, J = Hz, 1H), 7.35-7.26 (m, 3H), 7.29-7.22 (m, 2H), 6.81(s, 2H), 4.74 (q, J = 7.0 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H). 80 ¹H NMR(500 MHz, DMSO-d₆) δ 7.53-7.49 (m, 3H), 7.32-7.22 (m, 6H), 6.81 (s, 2H),4.70 (q, J = 7.0 Hz, 1H), 2.29 (p, J = 7.0 Hz, 1H), 1.25 (d, J = 6.5 Hz,3H), 1.12-1.08 (m, 2H), 0.84-0.80 (m, 2H). 81 ¹H NMR (500 MHz, DMSO-d₆)δ 7.72 (d, J = 7.0 Hz, 2H), 7.59-7.53 (m, 2H), 7.52-7.48 (m, 1H),7.36-7.30 (m, 2H), 7.26 (t, J = 7.5 Hz, 2H), 6.80 (s, 2H), 4.71 (q, J =7.0 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 82 ¹H NMR (500 MHz, DMSO-d₆) δ7.84-7.78 (m, 2H), 7.64-7.57 (m, 2H), 7.56-7.52 (m, 1H), 7.49-7.40 (m,2H), 7.36-7.33 (m, 1H), 6.80 (s, 2H), 4.65 (q, J = 7.0 Hz, 1H), 1.47 (d,J = 7.0 Hz, 3H). 83 ¹H NMR (500 MHz, DMSO-d₆) δ 7.53-7.52 (m, 1H),7.50-7.43 (m, 2H), 7.37-7.30 (m, 2H), 7.29-7.22 (m, 2H), 7.21 (dd, J =8.0, 2.0 Hz, 2H), 6.79 (s, 2H), 4.74 (q, J = 7.0 Hz, 1H), 1.54 (d, J =7.0 Hz, 3H). 84 ¹H NMR (500 MHz, DMSO-d₆) δ 7.60-7.48 (m, 2H), 7.16-7.13(m, 1H), 7.03 (dd, J = 7.5, 2.0 Hz, 1H), 6.78 (s, 2H), 4.63 (q, J = 7.0Hz, 1H), 3.87 (s, 3H), 1.48 (d, J = 7.0 Hz, 3H). 85 ¹H NMR (500 MHz,DMSO-d₆) δ 7.43-7.32 (m, 3H), 7.23-7.21 (m, 1H), 6.77 (s, 2H), 4.71 (q,J = 7.0 Hz, 1H), 2.82-2.71 (m, 1H), 2.60-2.49 (m, 1H), 1.52 (d, J = 7.0Hz, 3H), 1.20 (t, J = 8.0 Hz, 3H). 86 ¹H NMR (500 MHz, DMSO-d₆) δ7.79-7.71 (m, 4H), 6.77 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 1.54 (d, J =7.0 Hz, 3H). 87 ¹H NMR (500 MHz, DMSO-d₆) δ 7.54-7.42 (m, 4H), 6.78 (s,2H), 4.58 (q, J = 7.0 Hz, 1H), 1.56 (d, J = 7.0 Hz, 3H). 88 ¹H NMR (500MHz, DMSO-d₆) δ 10.16 (s, 1H), 7.73-7.67 (m, 2H), 7.56-7.50 (m, 2H),6.78 (s, 2H), 4.69 (q, J = 7.0 Hz, 1H), 4.48-4.76 (m, 1H), 3.79-3.77 (m,1H), 2.07 (s, 3H), 1.52 (d, J = 7.0 Hz, 3H), 1.08 (t, J = 8.0 Hz, 3H).89 ¹H NMR (500 MHz, DMSO-d₆) δ 7.49-7.42 (m, 2H), 7.39-7.33 (m, 2H),6.77 (s, 2H), 4.79 (q, J = 7.0 Hz, 1H), 2.45 (s, 3H), 2.39 (s, 3H), 1.47(d, J = 7.0 Hz, 3H). 90 ¹H NMR (500 MHz, DMSO-d₆) δ 7.22-7.16 (m, 2H),6.77 (s, 2H), 6.70-6.64 (m, 2H), 4.56 (q, J = 7.0 Hz, 1H), 3.02 (s, 6H),1.45 (d, J = 7.0 Hz, 3H). 91 ¹H NMR (500 MHz, DMSO-d₆) δ 7.29 (t, J =7.5 Hz, 2H), 7.24-7.18 (m, 2H), 7.04-6.97 (m, 2H), 6.94-6.92 (m, 1H),6.89-6.83 (m, 2H), 6.67 (s, 1H), 6.36 (s, 2H), 4.61 (q, J = 7.0 Hz, 1H),2.19 (s, 3H), 1.42 (d, J = 6.5 Hz, 3H). 92 ¹H NMR (500 MHz, DMSO-d₆) δ7.21-7.15 (m, 2H), 7.03-6.96 (m, 2H), 6.78 (s, 2H), 6.51 (dd, J = 15.0,1.0 Hz, 1H), 5.25-5.53 (m, 1H), 4.59 (q, J = 7.0 Hz, 1H), 4.47-4.45 (m,1H), 3.85-3.83 (m, 1H), 1.76 (dd, J = 6.5, 1.0 Hz, 3H), 1.46 (d, J = 7.0Hz, 3H), 1.36 (t, J = 8.0 Hz, 3H). 93 ¹H NMR (500 MHz, DMSO-d₆) δ 7.38(dd, J = 7.5, 2.0 Hz, 1H), 7.36-7.30 (m, 2H), 7.30-7.22 (m, 2H),7.25-7.17 (m, 1H), 7.10-7.08 (m, 1H), 6.81 (s, 2H), 6.73-6.71 (m, 1H),6.67-6.64 (m, 1H), 5.38 (s, 2H), 4.83 (q, J = 7.0 Hz, 1H), 4.28-4.21 (m,1H), 3.18-3.16 (m, 1H), 1.57 (d, J = 7.0 Hz, 3H). 94 ¹H NMR (500 MHz,DMSO-d₆) δ 9.40 (s, 1H), 7.35-7.23 (m, 5H), 6.79 (s, 2H), 5.06 (q, J =7.0 Hz, 1H), 4.46 (s, 2H), 1.60 (p, J = 7.0 Hz, 1H), 1.52 (d, J = 7.0Hz, 3H), 0.45-0.40 (m, 2H), 0.25-0.20 (m, 2H). 95 ¹H NMR (500 MHz,DMSO-d₆) δ 6.78 (s, 2H), 5.98-5.91 (m, 1H), 5.08-4.97 (m, 2H), 4.71 (q,J = 7.0 Hz, 1H), 2.80-2.79 (m, 2H), 1.41 (d, J = 7.0 Hz, 3H), 1.08 (p, J= 7.0 Hz, 1H), 0.20-0.16 (m, 2H), 0.11-0.01 (m, 2H). 96 ¹H NMR (500 MHz,DMSO-d₆) δ 7.43-7.40 (m, 2H), 7.33-7.24 (m, 3H), 7.17-7.10 (m, 2H),7.06-7.03 (m, 1H), 7.03-6.96 (m, 2H), 6.80 (s, 2H), 4.82 (q, J = 7.0 Hz,1H), 1.60 (d, J = 7.0 Hz, 3H). 97 ¹H NMR (500 MHz, DMSO-d₆) δ 7.39-7.36(m, 2H), 7.31-7.24 (m, 3H), 6.79 (s, 2H), 4.54 (q, J = 7.0 Hz, 1H),2.77-2.72(m, 1H), 2.46-2.41 (m, 1H), 1.37 (d, J = 7.0 Hz, 3H), 1.16 (t,J = 6.0 Hz, 3H). 98 ¹H NMR (500 MHz, DMSO-d₆) δ 8.21 (s, 1H), 7.66-7.58(m, 2H), 7.57-7.51 (m, 3H), 6.77 (s, 2H), 4.74 (q, J = 7.0 Hz, 1H),2.92-2.89 (m, 1H), 2.77-2.75 (m, 1H), 1.58-1.54 (m, 1H), 1.43 (d, J =7.0 Hz, 3H), 1.03-1.00 (m, 1H), 0.86 (t, J = 6.0 Hz, 3H). 99 ¹H NMR (500MHz, DMSO-d₆) δ 7.55-7.46 (m, 5H), 6.78 (s, 2H), 4.69 (q, J = 7.0 Hz,1H), 2.88 (s, 6H), 1.48 (d, J = 7.0 Hz, 3H). 100 ¹H NMR (500 MHz,DMSO-d₆) δ 9.40 (s, 1H), 7.22-7.16 (m, 2H), 7.13-7.11 (m, 2H), 6.78 (s,2H), 4.66 (q, J = 7.0 Hz, 1H), 4.37-4.30 (m, 1H), 4.19-4.16 (m, 1H),3.15-3.08 (m, 1H), 2.77-2.71 (m, 1H), 2.21 (s, 3H), 1.56 (d, J = 7.0 Hz,3H), 0.87 (t, J = 8.0 Hz, 3H). 101 ¹H NMR (500 MHz, DMSO-d₆) δ 9.40 (s,1H), 7.57-7.53 (m, 5H), 7.35-7.23 (m, 5H), 6.79 (s, 2H), 4.84 (q, J =7.0 Hz, 1H), 4.06-4.04 (m, 1H), 3.99-3.96 (m, 1H), 1.34 (d, J = 7.0 Hz,3H). 102 ¹H NMR (500 MHz, DMSO-d₆) δ 9.16 (s, 1H), 7.42-7.33 (m, 4H),6.46 (s, 2H), 4.70 (q, J = 7.0 Hz, 1H), 4.24-4.19 (m, 2H), 2.34 (s, 3H),1.43 (d, J = 7.0 Hz, 3H). 103 ¹H NMR (500 MHz, DMSO-d₆) δ 9.40 (s, 1H),7.28-7.22 (m, 2H), 6.93-6.87 (m, 2H), 4.58 (q, J = 7.0 Hz, 1H),4.15-4.13 (m, 1H), 3.82-3.80 (m, 1H), 3.79 (s, 3H), 2.61 (s, 3H), 1.57(d, J = 7.0 Hz, 3H). 104 ¹H NMR (500 MHz, DMSO-d₆) δ 9.40 (s, 1H),7.61-7.51 (m, 6H), 6.78 (s, 2H), 6.40-6.39 (m, 1H), 6.37-6.31 (m, 1H),4.95-4.94 (m, 1H), 4.77 (q, J = 7.0 Hz, 1H), 4.28-4.26 (m, 1H), 1.56 (d,J = 7.0 Hz, 3H). 105 ¹H NMR (500 MHz, DMSO-d₆) δ 8.21 (s, 1H), 7.61-7.50(m, 5H), 7.30-7.21 (m, 4H), 7.21-7.17 (m, 1H), 6.80 (s, 2H), 4.67 (q, J= 7.0 Hz, 1H), 3.27-3.12 (m, 2H), 3.01-2.98 (m, 1H), 2.43-2.38 (m, 1H),1.45(d, J = 7.0 Hz, 3H). 106 ¹H NMR (500 MHz, DMSO-d₆) δ 7.64-7.57 (m,2H), 7.41-7.39 (m, 2H), 7.22-7.13 (m, 2H), 6.75 (s, 2H), 4.95 (dd, J =10.0, 1.5 Hz, 1H), 4.76 (dd, J = 17, 1.5 Hz, 1H), 4.62 (q, J = 7.0 Hz,1H), 3.57 (s, 3H), 1.50 (d, J = 7.0 Hz, 3H). 107 ¹H NMR (500 MHz,DMSO-d₆) δ 7.57-7.51 (m, 3H), 7.41-7.27 (m, 7H), 6.83 (s, 2H), 5.15 (d,J = 12.5 Hz, 1H), 5.04 (d, J = 12.5 Hz, 1H), 4.52 (q, J = 7.0 Hz, 1H),1.50 (d, J = 7.0 Hz, 3H). 108 ¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H),6.81 (s, 2H), 6.64 (dd, J = 7.5, 1.5 Hz, 1H), 6.17 (t, J = 7.5 Hz, 1H),6.07 (dd, J = 7.5, 1.5 Hz, 1H), 5.48 (d, J = 12.5 Hz, 1H), 4.72 (d, J =12.5 Hz, 1H), 4.47 (q, J = 7.0 Hz, 1H), 2.72-2.65 (m, 1H), 2.43-2.36 (m,1H), 1.58 (d, J = 7.0 Hz, 3H), 0.96 (t, J = 8.0 Hz, 3H). 109 ¹H NMR (500MHz, DMSO-d₆) δ 8.07-7.96 (m, 4H), 7.85-7.83 (m, 1H), 7.66-7.57 (m, 2H),6.22 (s, 2H), 4.70 (q, J = 7.0 Hz, 1H), 3.56 (s, 3H), 1.55 (d, J = 7.0Hz, 3H). 110 ¹H NMR (500 MHz, DMSO-d₆) δ 5.95 (s, 1H), 4.68 (q, J = 7.0Hz, 1H), 2.70 (s, 3H), 2.43 (s, 3H), 2.40 (s, 3H), 1.49 (d, J = 7.0 Hz,3H). 111 ¹H NMR (500 MHz, DMSO-d₆) δ 6.12 (s, 1H), 4.57 (q, J = 7.0 Hz,1H), 3.75-3.73 (m, 1H), 3.25-3.22 (m, 1H), 2.45 (s, 3H), 2.43 (s, 3H),1.32 (d, J = 7.0 Hz, 3H), 1.26 (t, J = 8.0 Hz, 3H). 112 ¹H NMR (500 MHz,DMSO-d₆) δ 9.94 (s, 1H), 4.65 (q, J = 7.0 Hz, 1H), 2.45 (s, 3H), 2.43(s, 3H), 2.07 (s, 3H), 1.41 (d, J = 7.0 Hz, 3H). 113 ¹H NMR (500 MHz,DMSO-d₆) δ 10.47 (s, 1H), 7.53-7.51 (m, 1H), 6.43-6.41 (m, 1H),6.23-6.18 (m, 1H), 4.69 (q, J = 7.0 Hz, 1H), 3.87-3.85 (m, 1H),3.74-3.72 (m, 1H), 2.47 (s, 3H), 2.47 (s, 3H), 1.50 (d, J = 6.5 Hz, 3H).114 ¹H NMR (500 MHz, DMSO-d₆) δ 8.00-7.93 (m, 2H), 7.63-7.55 (m, 1H),7.55-7.53 (m, 2H), 4.60 (q, J = 7.0 Hz, 1H), 2.45 (s, 3H), 2.43 (s, 3H),1.56 (d, J = 7.0 Hz, 3H). 115 ¹H NMR (500 MHz, DMSO-d₆) δ 7.39-7.29 (m,4H), 7.28-7.25 (m, 1H), 6.22 (s, 1H), 4.93-4.89 (m, 1H), 4.65 (q, J =7.0 Hz, 1H), 4.27-4.25 (m, 1H), 2.51 (s, 3H), 2.50 (s,3H), 1.48 (d, J =7.0 Hz, 3H). 116 ¹H NMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 4.63 (q, J =7.0 Hz, 1H), 2.75-2.67 (m, 2H), 1.82-1.79 (m, 2H), 1.71-1.63 (m, 2H),1.49 (d, J = 7.0 Hz, 3H), 1.01-0.91 (m, 2H), 0.84-0.75 (m, 2H). 117 ¹HNMR (500 MHz, DMSO-d₆) δ 6.80 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H),2.69-2.57 (m, 2H), 2.45-2.37 (m, 2H), 1.47 (d, J = 6.5 Hz, 3H),1.13-1.03 (m, 2H), 0.74-0.66 (m, 2H). 118 ¹H NMR (500 MHz, DMSO-d₆)6.43-6.34 (m, 2H), 6.22 (s, 1H), 4.84 (d, J = 12.5 Hz, 1H), 4.70-4.62(m, 2H), 2.45 (s, 3H), 2.43 (s,3H), 1.51 (d, J = 7.0 Hz, 3H).

Several methods for preparing the compounds of the present invention aredetailedly illustrated in the following schemes and examples. Thestarting materials can be purchased commercially or can be prepared bymethods known in the literature or according to the detailedillustrations. Those skilled in the art will appreciate that othersynthetic routes can also be utilized to synthesize the compounds of thepresent invention. Although specific starting materials and conditionsin the synthetic route have been described below, they can be easilyreplaced with other similar starting materials and conditions, andvarious isomers of compounds and the like produced by variations orvariants of the preparation methods of the present invention areincluded in the scope of the present invention. Additionally, thepreparation methods described below can be further modified inaccordance with the present disclosure, using conventional chemicalmethods well known to those skilled in the art. For example, appropriategroups are protected during the reaction, and the like.

The method examples are provided below to facilitate a furtherunderstanding of the preparation method of the present invention, andthe specific materials, types and conditions used are determined to befurther description of the present invention and are not intended tolimit its rational scope. The reagents used for synthesizing thefollowing compounds indicated in the table below are either commerciallyavailable or can be readily prepared by those skilled in the art.

The examples of representative compounds are as follows, the syntheticmethods of other compounds are similar, and will not be described indetail here.

1. Synthesis of Compound 3

Compound 3-1 (300 mg, 1.19 mmol), compound 3-2 (236 mg, 1.19 mmol), DCC(369 mg, 1.79 mmol) and dehydrated dichloromethane (20 ml) were added toa 50 ml round-bottom flask, reacted for 12 hours at room temperature.After completed reaction of the starting materials according to LC-MSdetection, the reaction solution was concentrated, and separated bycolumn chromatography to obtain compound 3 (180 mg, yield 35%).

2. Synthesis of Compound 53

(1) Compound 53-1 (400 mg, 1.70 mmol), compound 53-2 (680 mg), acatalytic amount of TBAB (10 mg) and DMF (10 mL) were added to a 50 mlround-bottom flask, heated to 85° C. and reacted for 12 hours. Aftercompleted reaction of the starting materials according to LC-MSdetection, the reaction solution was cooled to room temperature, andextracted with water (100 ml) and MTBE (50 ml×2). The organic phase wasdried, concentrated, and separated by column chromatography to obtaincompound 53-3 (360 mg, yield 47%).

(2) Compound 53-3 (0.36 g, 1.17 mmol) and methanol (20 mg) were added toa 100 ml single mouth flask. Lithium hydroxide (48 mg, 2.0 mmol) wasdissolved in 2 ml water and slowly added dropwise into the single mouthflask at room temperature. Agitated for 12 hours at room temperature.After completed reaction of the starting materials according to LC-MSdetection, adjusted with 0.5M dilute hydrochloric acid to pH=5-6,concentrated and then extracted with water and ethyl acetate. Theorganic phase was dried and concentrated to obtain compound 53-4 (300mg).

(3) Compound 53-4 (300 mg, 0.87 mmol), compound a (64 mg, 0.87 mmol),DCC (289 mg, 1.31 mmol) and dehydrated dichloromethane (20 ml) wereadded to a 50 ml round-bottom flask, reacted for 12 hours at roomtemperature. After completed reaction of the starting materialsaccording to LC-MS detection, the reaction solution was concentrated,and separated by column chromatography to obtain compound 53 (110 mg,yield 32%).

3. Synthesis of Compound 67

Compound b (400 mg, 1.49 mmol), compound a (109 mg, 1.49 mmol), DCC (459mg, 2.24 mmol) and dehydrated DCM (20 ml) were added to a 100 mlround-bottom flask, reacted for 12 hours at room temperature. Aftercompleted reaction of the starting materials according to LC-MSdetection, the reaction solution was concentrated, and separated bycolumn chromatography to obtain compound 67 (150 mg, yield 31%), as awhite solid.

4. Synthesis of Compound 113

(1) Compound 113-1 (500 mg, 1.77 mmol), potassium carbonate (488 mg,3.53 mmol), 113-2 (427 mg, 2.65 mmol), a catalytic amount of DMAP (10mg) and acetonitrile (20 ml) were added to a 50 ml round-bottom flask.Heated to 80° C. and reacted for 12 hours. After completed reaction ofthe starting materials according to LC-MS detection, the reactionsolution was cooled to room temperature, concentrated, and separated bycolumn chromatography to obtain compound 113-3 (400 mg, yield 62%), as acolorless oil.

(2) Compound 113-3 (400 mg, 1.10 mmol) was dissolved in 20 mL methanol.LiOH solution (46.2 mg, 1.10 mmol) was dissolved in 5 ml water andslowly added dropwise into the reaction flask, reacted for 12 hours atroom temperature. After completed reaction of the starting materialsaccording to LC-MS detection, adjusted with 0.5M dilute hydrochloricacid to neutral, concentrated to remove methanol and then washed withethyl acetate (10 mL×3) and water (100 mL). The organic phase was driedand concentrated to obtain compound 113-4 (300 mg, yield 78%).

(3) Compound 113-4 (300 mg, 0.86 mmol), compound a (63 mg, 0.86 mmol),DCC (291 mg, 1.29 mmol) and dehydrated DCM (20 ml) were added to a 50 mlround-bottom flask, reacted for 12 hours at room temperature. Aftercompleted reaction of the starting materials according to LC-MSdetection, the reaction solution was concentrated, and separated bycolumn chromatography to obtain compound 113 (100 mg, yield 29%).

Biological Activity Evaluation:

The activity level standard of plants destruction (i. e. growthinhibition rate) is as follows:

Level 5: the growth inhibition rate is greater than 85%;

Level 4: the growth inhibition rate is equal to or greater than 60% andless than 85%;

Level 3: the growth inhibition rate is equal to or greater than 40% andless than 60%;

Level 2: the growth inhibition rate is equal to or greater than 20% andless than 40%;

Level 1: the growth inhibition rate is equal to or greater than 5% andless than 20%;

Level 0: the growth inhibition rate is less than 5%;

The above described growth inhibition rate is fresh weight inhibitionrate.

Post-emergence test experiment: Monocotyledonous and dicotyledonous weedseeds and main crop seeds (i. e. wheat, corn, rice, soybean, cotton,oilseed, millet and sorghum.) were put into a plastic pot loaded withsoil. Then covered with 0.5-2 cm soil, the seeds were allowed to grow ingood greenhouse environment. The test plants were treated at 2-3 leafstage 2 weeks after sowing. The test compounds of the invention weredissolved with acetone respectively, then added with tween-80, and using1.5 liters per hectare of an emulsible concentrate of methyl oleate as asynergist, and diluted by certain amount of water to certainconcentration. The solution was sprayed to the plants with a sprayer.Then the plants were cultured for 3 weeks in the greenhouse, and theexperiment result of weed controlling effect was listed in tables 3-4.

TABLE 3 Activity test results of compounds (1000 g a.i./ha) DigitariaEchinochloa Setaria Leptochloa Monochoria Galium Murdannia No.sanguinalis crusgalli viridis chinensis Vaginalis spurium triquetra 1 55 5 5 5 5 5 2 5 5 5 5 5 5 5 3 5 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 5 55 5 6 5 5 5 5 5 5 5 7 5 5 5 5 5 5 5 8 5 5 5 5 5 5 5 9 5 5 5 5 5 5 5 10 55 5 5 5 5 5 11 5 5 5 5 5 5 5 12 5 5 5 5 5 5 5 13 5 5 5 5 5 5 5 14 5 5 55 5 5 5 15 5 5 5 5 5 5 5 16 5 5 5 5 5 5 5 17 5 5 5 5 5 5 5 18 5 5 5 5 55 5 19 5 5 5 5 5 5 5 20 5 5 5 5 5 5 5 21 5 5 5 5 5 5 5 22 5 5 5 5 5 5 523 5 5 5 5 5 5 5 24 5 5 5 5 5 5 5 25 5 5 5 26 5 5 5 27 5 5 5 28 5 5 5 295 5 5 30 5 5 5 31 5 5 5 32 5 5 5 33 5 5 5 34 5 5 5 35 5 5 5 36 5 5 5 375 5 5 38 5 5 5 39 5 5 5 40 5 5 5 41 5 5 5 42 5 5 5 43 5 5 5 44 5 5 5 455 5 5 46 5 5 5 47 5 5 5 48 5 5 5 49 5 5 5 50 5 5 5 51 5 5 5 52 5 5 5 535 5 5 54 5 5 5 55 5 5 5 56 5 5 5 57 5 5 5 58 5 5 5 59 5 5 5 60 5 5 5 615 5 5 62 5 5 5 63 5 5 5 64 5 5 5 65 5 5 5 66 5 5 5 67 5 5 5 5 5 5 5 68 55 5 5 5 5 5 69 5 5 5 5 5 5 5 70 5 5 5 5 5 5 5 71 5 5 5 5 5 5 5 72 5 5 55 5 5 5 73 5 5 5 5 5 5 5 74 5 5 5 5 5 5 5 75 5 5 5 5 5 5 5 76 5 5 5 5 55 5 77 5 5 5 5 5 5 5 78 5 5 5 5 5 5 5 79 5 5 5 5 5 5 5 80 5 5 5 5 5 5 581 5 5 5 5 5 5 5 82 5 5 5 5 5 5 5 83 5 5 5 5 5 5 5 84 5 5 5 5 5 5 5 85 55 5 5 5 5 5 86 5 5 5 5 5 5 5 87 5 5 5 5 5 5 5 88 5 5 5 5 5 5 5 89 5 5 55 5 5 5 90 5 5 5 5 5 5 5 91 5 5 5 5 5 5 5 92 5 5 5 5 5 5 5 93 5 5 5 5 55 5 94 5 5 5 5 5 5 5 95 5 5 5 5 5 5 5 96 5 5 5 5 5 5 5 97 5 5 5 5 5 5 598 5 5 5 5 5 5 5 99 5 5 5 5 5 5 5 100 5 5 5 5 5 5 5 101 5 5 5 5 5 5 5102 5 5 5 5 5 5 5 103 5 5 5 5 5 5 5 104 5 5 5 5 5 5 5 105 5 5 5 5 5 5 5106 5 5 5 5 5 5 5 107 5 5 5 5 5 5 5 108 5 5 5 5 5 5 5 109 5 5 5 5 5 5 5110 5 5 5 5 5 5 5 111 5 5 5 5 5 5 5 112 5 5 5 5 5 5 5 113 5 5 5 5 5 5 5114 5 5 5 5 5 5 5 115 5 5 5 5 5 5 5 116 5 5 5 5 5 5 5 117 5 5 5 5 5 5 5118 5 5 5 5 5 5 5

TABLE 4 Test results of post-emergence weeds Japonica Indica Cyperus No.rice rice iria 4 0 0 5 12 0 0 5 67 0 0 5 68 0 0 5 69 0 0 5 70 0 0 5 75 00 5 84 0 0 5 87 0 0 5 88 0 0 5 90 0 0 5 92 0 0 5 100 0 0 5 104 0 0 5 1170 0 5 Control compound 3 3 5 A (600 g a.i./ha) Control compound 2 3 4 A(300 g a.i./ha) Note: the application dose was active ingredient 600g/ha, plus water 450 kg/ha.

Control Compound A:

It is observed from the testing that the compounds of the presentinvention have excellent selectivity to rice, regardless of japonica orindica rice, whereas the control compound has great inhibition to ricewhich results to decrease of biomass and swelling of root thus notavailable for commercial production. As observed, the present inventionhas unexpected high efficacy.

Experiment on weed effect in pre-emergence stage Seeds ofmonocotyledonous and dicotyledonous weeds and main crops (e. g. wheat,corn, rice, soybean, cotton, oilseed, millet and sorghum) were put intoa plastic pot loaded with soil and covered with 0.5-2 cm soil. The testcompounds of the present invention was dissolved with acetone, thenadded with tween-80, diluted by a certain amount of water to reach acertain concentration, and sprayed immediately after sowing. Theobtained seeds were incubated for 4 weeks in the greenhouse afterspraying and the test results were observed. It was observed that theherbicide mostly had excellent effect at the application rate of 250 ga.i./ha, especially to weeds such as Echinochloa crusgalli, Digitariasanguinalis and Abutilon theophrasti, etc. Many compounds had goodselectivity for corn, wheat, rice, soybean, oilseed rape, etc.

Through experiments, we found that the compounds of the presentinvention generally had better weed control effects, especially formajor gramineous weeds such as Echinochloa crusgalli, Digitariasanguinalis, and Setaria viridis, which are widely occurring in cornfields, rice fields and wheat fields, and major broad-leaved weeds suchas Abutilon theophrasti, Rorippa indica and Bidens pilosa, and hadexcellent commercial value. In particular, we noticed that they hadextremely high activity against broad-leaved weeds, such as Rorippaindica, Descurainia sophia, Capsella bursa-pastoris, Lithospermumarvense, Galium spurium and Stellaria media, which were resistant to ALSinhibitors.

Transplanted Rice Safety Evaluation and Weed Control Effect Evaluationin Rice Field:

Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds ofScirpus juncoides, Sagittaria trifolia and Monochoria vaginalis weresowed and gently covered with soil, then left to stand still ingreenhouse in the state of 0.5-1 cm of water storage. The tuber ofSagittaria trifolia was planted in the next day or 2 days later. It waskept at 3-4 cm of water storage thereafter. The weeds were treated bydripping the WP or SC water diluents prepared according to the commonpreparation method of the compounds of the present invention withpipette homogeneously to achieve specified effective amount when Scirpusjuncoides, and Monochoria vaginalis reached 0.5 leaf stage andSagittaria trifolia reached the time point of primary leaf stage.

In addition, the rice field soil that loaded into the 1/1,000,000 ha potwas leveled to keep water storage at 3-4 cm depth. The 3 leaf stage rice(japonica rice) was transplanted at 3 cm of transplanting depth the nextday. The compound of the present invention was treated by the same wayafter 5 days of transplantation.

The fertility condition of Scirpus juncoides, Sagittaria trifolia andMonochoria vaginalis 14 days after the treatment of the compound of theinvention and the fertility condition of rice 21 days after thetreatment of the compound of the invention respectively with the nakedeye. Evaluate the weed control effect with 0-5 activity standard level.Many compounds show excellent activity and selectivity.

TABLE 5 Test results of activity and safety (1000 g a.i./ha) MonochoriaScirpus Sagittaria No. Rice Vaginalis juncoides trifolia 1 0 5 4 4 2 0 54 4 3 0 5 4 5 4 0 5 4 5 70 0 5 4 4 84 0 5 4 4 88 0 5 4 4 Note: The seedsof Scirpus juncoides, Sagittaria trifolia and Monochoria vaginalis werecollected from Heilongjing Province of China. Tests indicated that theweeds were resistant to common rate of pyrazosulfuron-ethyl andpenoxsulam.

It can be seen from the experiments that the compounds of the presentinvention had excellent activity against weeds having an anti-ALSinhibiting activity which cause a serious challenge in production, andcan solve the increasingly serious problem of resistance.

At the same time, it is found after several tests that the compound andthe composition of the present invention have good selectivity to manygramineae weeds such as Zoysia japonica, Cynodon dactylon, Festucaelata, Poa annua, Lolium perenne and Paspalum vaginatum etc, and is ableto control many important gramineous weeds and broad-leaved weeds. Thecompound also shows excellent selectivity and commercial value in thetests on wheat, corn, rice, sugarcane, soybean, cotton, oil sunflower,potato, orchards and vegetables in different herbicide applicationmethods.

1. A pyridyloxy carboxylic oxime derivative represented by formula I,

wherein, A, B each independently represent halogen; or alkyl orcycloalkyl with or without halogen; C represents hydrogen, halogen,alkyl or haloalkyl; Q represents halogen, cyano, cyanoalkyl,hydroxyalkyl, amino, nitro, formyl; alkyl, alkenyl, alkynyl, cycloalkyl,alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylaminoalkyl oralkoxyalkyl with or without halogen; or unsubstituted or substitutedaryl, heteroaryl, arylalkyl or heteroarylalkyl; R₁ and R₂ independentlyrepresent H, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl,cycloalkyl, alkoxy, acyloxy, alkylthio, unsubstituted or substitutedaryl, unsubstituted or substituted benzyl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted aryloxy, unsubstituted orsubstituted arylthio, unsubstituted or substituted heteroaryloxy,unsubstituted or substituted heteroarylthio or the group represented bythe formula of —COR₅, wherein, R₅ represents alkyl, haloalkyl, alkenyl,cycloalkyl, alkoxy, alkenoxy, cycloalkoxy, alkylthio, alkenylthio,cycloalkylthio, unsubstituted or substituted benzyl, unsubstituted orsubstituted aryl, unsubstituted or substituted heteroaryl, unsubstitutedor substituted aryloxy, unsubstituted or substituted heteroaryloxy,unsubstituted or substituted arylalkyloxy, unsubstituted or substitutedheteroarylalkyloxy, unsubstituted or substituted arylalkylthio,unsubstituted or substituted heteroarylalkylthio, unsubstituted orsubstituted benzylthio, unsubstituted or substituted arylthio,unsubstituted or substituted heteroarylthio, or amino which isoptionally substituted by alkyl, acyl, acyloxy, unsubstituted orsubstituted aryl, unsubstituted or substituted heteroaryl, unsubstitutedor substituted arylalkyl or unsubstituted or substitutedheteroarylalkyl; or R₁ and R₂ are linked to form a 5- or 6-membersaturated or unsaturated ring; M represents nitro or NR₃R₄, wherein R₃represents H; alkyl, alkenyl or alkynyl optionally substituted by 1-2R₁₁; —COR₁₂, nitro, OR₁₃, SO₂R₁₄, NR₁₅R₁₆, N═CR₁₇R₁₈, alkylcarbamoyl,dialkylcarbamoyl, trialkylsilyl or dialkylphosphono; R₄ represents H;alkyl optionally substituted by 1-2 R₁₁; or —COR₁₂; or NR₃R₄ representsN═CR₂₁NR₂₂R₂₃, N═CR₂₄OR₂₅; or a 5- or 6-membered saturated orunsaturated ring with or without oxygen atom, sulfur atom, or othernitrogen atom, which is unsubstituted or substituted by 1-2 groupsindependently selected from the group consisting of halogen, alkyl,alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino,dialkylamino and alkoxycarbonyl; wherein R₁₁ independently representshalogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino,alkylamino, dialkylamino, alkoxycarbonyl; or unsubstituted orsubstituted aryl or heteroaryl; R₁₂ represents H, alkyl, haloalkyl,alkoxy, phenyl, phenoxy or benzyloxy; R₁₃ represents H, alkyl,haloalkyl, phenyl, benzyl or CHR₃₁C(O)OR₃₂; R₃₁ represents H, alkyl oralkoxy; R₃₂ represents H, alkyl or benzyl; R₁₄ represents alkyl orhaloalkyl; R₁₅ represents H, alkyl, formyl, alkylacyl, haloalkylacyl,alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl;R₁₆ represents H or alkyl; R₁₇ represents H, alkyl; or phenyl that isunsubstituted or substituted by 1-3 groups selected from the groupconsisting of halogen, alkyl and alkoxy; R₁₈ represents H or alkyl; orN═CR₁₇R₁₈ represents

R₂₁, R₂₄ each independently represent H or alkyl; R₂₂, R₂₃ eachindependently represent H or alkyl; or NR₂₂R₂₃ represents a 5- or6-membered saturated or unsaturated ring with or without oxygen atom,sulfur atom, or other nitrogen atom; R₂₅ represents alkyl.
 2. Thepyridyloxy carboxylic oxime derivative according to claim 1, wherein A,B each independently represent halogen; or C1-C8 alkyl or C3-C8cycloalkyl with or without halogen; C represents hydrogen, halogen,C1-C8 alkyl or halo C1-C8 alkyl; Q represents halogen, cyano, cyanoC1-C8 alkyl, hydroxy C1-C8 alkyl, amino, nitro, formyl; C1-C8 alkyl,C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylaminoC1-C8 alkyl or C1-C8 alkoxy C1-C8 alkyl with or without halogen; orunsubstituted or substituted aryl, heteroaryl, aryl C1-C8 alkyl orheteroaryl C1-C8 alkyl; R₁ and R₂ independently represent H, halogen,cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8cycloalkyl, C1-C8 alkoxy, C1-C8 acyloxy, C1-C8 alkylthio, unsubstitutedor substituted aryl, unsubstituted or substituted benzyl, unsubstitutedor substituted heteroaryl, unsubstituted or substituted aryloxy,unsubstituted or substituted arylthio, unsubstituted or substitutedheteroaryloxy, unsubstituted or substituted heteroarylthio or the grouprepresented by the formula of —COR₅, wherein, R₅ represents C1-C8 alkyl,halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8alkenoxy, C3-C8 cycloalkoxy, C1-C8 alkylthio, C2-C8 alkenylthio, C3-C8cycloalkylthio, unsubstituted or substituted benzyl, unsubstituted orsubstituted aryl, unsubstituted or substituted heteroaryl, unsubstitutedor substituted aryloxy, unsubstituted or substituted heteroaryloxy,unsubstituted or substituted aryl C1-C8 alkyloxy, unsubstituted orsubstituted heteroaryl C1-C8 alkyloxy, unsubstituted or substituted arylC1-C8 alkylthio, unsubstituted or substituted heteroaryl C1-C8alkylthio, unsubstituted or substituted benzylthio, unsubstituted orsubstituted arylthio, unsubstituted or substituted heteroarylthio, oramino which is optionally substituted by C1-C8 alkyl, C1-C8 acyl, C1-C8acyloxy, unsubstituted or substituted aryl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted aryl C1-C8 alkyl orunsubstituted or substituted heteroaryl C1-C8 alkyl; or R₁ and R₂ arelinked to form a 5- or 6-member saturated carbocyclic ring; M representsnitro or NR₃R₄, wherein R₃ represents H; C1-C8 alkyl, C2-C8 alkenyl orC2-C8 alkynyl optionally substituted by 1-2 R₁₁; —COR₁₂, nitro, OR₁₃,SO₂R₁₄, NR₁₅R₁₆, N═CR₁₇R₁₈, C1-C8 alkylcarbamoyl, di-C1-C8alkylcarbamoyl, tri-C1-C8 alkylsilyl or di-C1-C8 alkylphosphono; R₄represents H; C1-C8 alkyl optionally substituted by 1-2 R₁₁; or —COR₁₂;or NR₃R₄ represents N═CR₂₁NR₂₂R₂₃, N═CR₂₄OR₂₅; or

that is unsubstituted or substituted by 1-2 groups independentlyselected from the group consisting of halogen, C1-C8 alkyl, C1-C8alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino,C1-C8 alkylamino, di-C1-C8 alkylamino and C1-C8 alkoxycarbonyl; whereinR₁₁ independently represents halogen, hydroxy, C1-C8 alkoxy, halo C1-C8alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino,di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl; or phenyl, naphthyl,

that is unsubstituted or substituted by 1-3 groups selected from thegroup consisting of halogen, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxyand nitro; R₁₂ represents H, C1-C18 alkyl, halo C1-C8 alkyl, C1-C8alkoxy, phenyl, phenoxy or benzyloxy; R₁₃ represents H, C1-C8 alkyl,halo C1-C8 alkyl, phenyl, benzyl or CHR₃₁C(O)OR₃₂; R₃₁ represents H,C1-C8 alkyl or C1-C8 alkoxy; R₃₂ represents H, C1-C8 alkyl or benzyl;R₁₄ represents C1-C8 alkyl or halo C1-C8 alkyl; R₁₅ represents H, C1-C8alkyl, formyl, C1-C8 alkylacyl, halo C1-C8 alkylacyl, C1-C8alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl;R₁₆ represents H or C1-C8 alkyl; R₁₇ represents H, C1-C8 alkyl; orphenyl that is unsubstituted or substituted by 1-3 groups selected fromthe group consisting of halogen, C1-C8 alkyl and C1-C8 alkoxy; R₁₈represents H or C1-C8 alkyl; or N═CR₁₇R₁₈ represents

R₂₁, R₂₄ each independently represent H or C1-C8 alkyl; R₂₂, R₂₃ eachindependently represent H or C1-C8 alkyl; or NR₂₂R₂₃ represents

R₂₅ represents C1-C8 alkyl; the term “aryl” refers to phenyl ornaphthyl; the term “heteroaryl” refers to an aromatic ring groupcontaining 3 to 6 ring atoms and is optionally fused via benzo ring, 1to 4 heteroatoms in the ring atoms being selected from oxygen, nitrogenand sulfur, for example,

which is optionally substituted by at least one group selected from thegroup consisting of halogen, nitro, cyano, thiocyano, hydroxy, carboxy,mercapto, formyl; phenyl, benzyl, benzyloxy or phenoxy that isunsubstituted or substituted by at least one group from the groupconsisting of halogen, alkyl and alkoxy; alkyl, alkenyl, alkynyl,cycloalkyl, cycloalkylalkyl, OR″, SR″, -alkyl-OR″, -alkyl-SR″, COR″,COOR″, COSR″, SOR″, SO₂R″, OCOR″ or SCOR″ with or without halogen; andamino or aminocarbonyl substituted by one or two groups selected fromthe group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkylalkyl, phenyl, benzyl, benzyloxy, phenoxy, COR″, COOR″, SO₂R″and OR″; R′ each independently represents hydrogen, nitro, hydroxy,amino; or alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl,cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy,alkoxyalkyl, alkoxycarbonyl, alkylthiocarbonyl, alkylsulfonyl,alkylsulfonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylacyloxy,alkylamino, alkylaminocarbonyl, alkoxyaminocarbonyl,alkoxycarbonylalkyl, alkylaminocarbonylalkyl, trialkylsilyl ordialkylphosphono with or without halogen; R″ each independentlyrepresents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl orcycloalkylalkyl.
 3. The pyridyloxy carboxylic oxime derivative accordingto claim 2, wherein A, B each independently represent halogen; or C1-C6alkyl or C3-C6 cycloalkyl with or without halogen; C representshydrogen, halogen, C1-C6 alkyl or halo C1-C6 alkyl; Q representshalogen, cyano, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, amino, nitro,formyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl,C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6 alkylamino C1-C6 alkyl or C1-C6 alkoxy C1-C6 alkylwith or without halogen; or unsubstituted or substituted aryl,heteroaryl, aryl C1-C6 alkyl or heteroaryl C1-C6 alkyl; R₁ and R₂independently represent H, cyano, C1-C6 alkyl, halo C1-C6 alkyl, C2-C6alkenyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 acyloxy, C1-C6 alkylthio,unsubstituted or substituted aryl, unsubstituted or substituted benzyl,unsubstituted or substituted heteroaryl, unsubstituted or substitutedaryloxy, unsubstituted or substituted arylthio, unsubstituted orsubstituted heteroaryloxy, unsubstituted or substituted heteroarylthioor the group represented by the formula of —COR₅, wherein, R₅ representsC1-C6 alkyl, halo C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C1-C6alkoxy, C2-C6 alkenoxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, C2-C6alkenylthio, C3-C6 cycloalkylthio, unsubstituted or substituted benzyl,unsubstituted or substituted aryl, unsubstituted or substitutedheteroaryl, unsubstituted or substituted aryloxy, unsubstituted orsubstituted heteroaryloxy, unsubstituted or substituted aryl C1-C6alkyloxy, unsubstituted or substituted heteroaryl C1-C6 alkyloxy,unsubstituted or substituted aryl C1-C6 alkylthio, unsubstituted orsubstituted heteroaryl C1-C6 alkylthio, unsubstituted or substitutedbenzylthio, unsubstituted or substituted arylthio, unsubstituted orsubstituted heteroarylthio, or amino which is optionally substituted byC1-C6 alkyl, C1-C6 acyl, C1-C6 acyloxy, unsubstituted or substitutedaryl, unsubstituted or substituted heteroaryl, unsubstituted orsubstituted aryl C1-C6 alkyl or unsubstituted or substituted heteroarylC1-C6 alkyl; or R₁ and R₂ are linked to form a 5- or 6-member saturatedcarbocyclic ring; M represents nitro or NR₃R₄, wherein R₃ represents H;C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl optionally substituted by1-2 R₁₁; —COR₁₂, nitro, OR₁₃, SO₂R₁₄, NR₁₅R₁₆, N═CR₁₇R₁₈, C1-C6alkylcarbamoyl, di-C1-C6 alkylcarbamoyl, tri-C1-C6 alkylsilyl ordi-C1-C6 alkylphosphono; R₄ represents H; C1-C6 alkyl optionallysubstituted by 1-2 R₁₁; or —COR₁₂; or NR₃R₄ represents N═CR₂₁NR₂₂R₂₃,N═CR₂₄OR₂₅; or

that is unsubstituted or substituted by 1-2 groups independentlyselected from the group consisting of halogen, C1-C6 alkyl, C1-C6alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino,C1-C6 alkylamino, di-C1-C6 alkylamino and C1-C6 alkoxycarbonyl; whereinR₁₁ independently represents halogen, hydroxy, C1-C6 alkoxy, halo C1-C6alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino,di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl; or phenyl, naphthyl,

that is unsubstituted or substituted by 1-3 groups selected from thegroup consisting of halogen, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxyand nitro; R₁₂ represents H, C1-C14 alkyl, halo C1-C6 alkyl, C1-C6alkoxy, phenyl, phenoxy or benzyloxy; R₁₃ represents H, C1-C6 alkyl,halo C1-C6 alkyl, phenyl, benzyl or CHR₃₁C(O)OR₃₂; R₃₁ represents H,C1-C6 alkyl or C1-C6 alkoxy; R₃₂ represents H, C1-C6 alkyl or benzyl;R₁₄ represents C1-C6 alkyl or halo C1-C6 alkyl; R₁₅ represents H, C1-C6alkyl, formyl, C1-C6 alkylacyl, halo C1-C6 alkylacyl, C1-C6alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl;R₁₆ represents H or C1-C6 alkyl; R₁₇ represents H, C1-C6 alkyl; orphenyl that is unsubstituted or substituted by 1-3 groups selected fromthe group consisting of halogen, C1-C6 alkyl and C1-C6 alkoxy; R₁₈represents H or C1-C6 alkyl; or N═CR₁₇R₁₈ represents

R₂₁, R₂₄ each independently represent H or C1-C6 alkyl; R₂₂, R₂₃ eachindependently represent H or C1-C6 alkyl; or NR₂₂R₂₃ represents

R₂₅ represents C1-C6 alkyl; the term “aryl” refers to phenyl ornaphthyl; the term “heteroaryl” refers to

which is substituted by 0, 1, 2 or 3 groups selected from the groupconsisting of halogen, nitro, cyano, thiocyano, hydroxy, carboxy,mercapto, formyl; phenyl, benzyl, benzyloxy or phenoxy that isunsubstituted or substituted by at least one group from the groupconsisting of halogen, C1-C6 alkyl and C1-C6 alkoxy; C1-C6 alkyl, C2-C6alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl,OR″, SR″, —(C1-C6)alkyl-OR″, —(C1-C6)alkyl-SR″, COR″, COOR″, COSR″,SOR″, SO₂R″, OCOR″ or SCOR″ with or without halogen; and amino oraminocarbonyl substituted by one or two groups selected from the groupconsisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, phenyl, benzyl, benzyloxy,phenoxy, COR″, COOR″, SO₂R″ and OR″; R′ each independently representshydrogen, nitro, hydroxy, amino; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6alkynyl, C3-C6 cycloalkyl, C3-C6 cyclo alkenyl, C3-C6 cycloalkyl C1-C6alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6cycloalkyloxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl C1-C6 alkyl,C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6alkoxyaminocarbonyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6alkylaminocarbonyl C1-C6 alkyl, tri-C1-C6 alkylsilyl, di-C1-C6alkylphosphono with or without fluoro, chloro or bromo; R″ eachindependently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C6 alkyl.
 4. Thepyridyloxy carboxylic oxime derivative according to claim 3, wherein A,B each independently represent halogen, C1-C6 alkyl, halo C1-C6 alkyl orC3-C6 cycloalkyl; C represents hydrogen, halogen, C1-C6 alkyl or haloC1-C6 alkyl; Q represents C1-C6 alkyl, halo C1-C6 alkyl, C3-C6cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, cyano, amino, nitro,formyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxycarbonyl, hydroxyC1-C6 alkyl, C1-C6 alkoxy C1-C2 alkyl, cyano C1-C2 alkyl, C1-C6alkylamino C1-C2 alkyl, benzyl, naphthyl, furyl, thienyl, thiazolyl,pyridyl, pyrimidinyl;

that is unsubstituted or substituted by C1-C6 alkyl; or phenyl that isunsubstituted or substituted by at least one group selected from thegroup consisting of C1-C6 alkyl, halo C1-C6 alkyl, halogen and C1-C6alkoxy; R′ represents C1-C6 alkyl or halo C1-C6 alkyl. R₁ and R₂independently represent H, halogen, C1-C6 alkyl, halo C1-C6 alkyl, C3-C6cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, cyano, nitro,benzyl, phenoxy, phenylthio, naphthyl; phenyl that is unsubstituted orsubstituted by one or more group selected from the group consisting ofhalogen, C1-C6 alkyl, halo C1-C6 alkyl, C3-C6 cycloalkyl, nitro, cyano,C1-C6 alkoxy, C1-C6 alkylthio, C2-C6 alkenyloxy, amino, C1-C6alkylamino, C1-C6 alkylcarbonylamino, C1-C6 alkylphenylamino andphenoxyamino; or the group represented by the formula of —COR₅, wherein,R₅ represents C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C2-C6alkenoxy, phenoxy, benzyloxy, pyrrolyl C1-C2 alkyloxy, C1-C6 alkylamino,C1-C6 alkylamino, C1-C6 alkylphenylamino, furyl C1-C2 alkylamino,phenylethyleneamino; or benzylamino that is unsubstituted or substitutedby C1-C6 alkyl, halogen or C1-C6 alkoxy; Or

represents

M represents amino, C1-C6 alkylamino, C1-C6 alkylcarbonylamino,phenylcarbonylamino, benzylamino; or furylmethyleneamino that isunsubstituted or substituted by halo C1-C6 alkyl.
 5. The pyridyloxycarboxylic oxime derivative according to claim 4, wherein A, B eachindependently represent fluoro, chloro, bromo, iodo, methyl, ethyl,propyl, isopropyl, trifluoromethyl or cyclopropyl; C representshydrogen, fluoro, chloro, bromo, iodo, methyl or trifluoromethyl; Qrepresents methyl, ethyl, propyl, isopropyl, cyclopropyl, vinyl,ethynyl, fluoro, chloro, bromo, cyano, amino, nitro, formyl, methoxy,methylthio, methoxycarbonyl, monochloromethyl, monofluoromethyl,difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl,hydroxymethyl,

benzyl, naphthyl, furyl, thienyl, thiazolyl, pyridyl, pyrimidinyl;

that is unsubstituted or substituted by methyl; or phenyl that isunsubstituted or substituted by at least one group selected from thegroup consisting of methyl, trifluoromethyl, chloro and methoxy; R′represents methyl, ethyl or difluoromethyl; R₁ and R₂ independentlyrepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl,isopropyl, n-butyl, tert-butyl, cyclopropyl, allyl, 2-chloroethyl,methylthio, ethylthio, ethoxy, cyano, nitro, benzyl, phenoxy,phenylthio, naphthyl; phenyl that is unsubstituted or substituted by oneor more group selected from the group consisting of fluoro, chloro,ethyl, cyclopropyl, trifluoromethyl, nitro, cyano, methoxy, methylthio,propenyloxy, amino, dimethylamino, acetamido, phenoxyamino andmethylphenylamino; or the group represented by the formula of —COR₅,wherein, R₅ represents methyl, ethyl, methoxy, ethoxy, methylthio,vinyloxy, phenoxy, benzyloxy, pyrrolylmethyleneoxy, dimethylamino,propylamino, methylphenylamino, furylmethyleneamino, phenethylenylamino,or benzylamino that is unsubstituted or substituted by methyl, chloro ormethoxy; Or

represents

M represents NH₂,


6. The pyridyloxy carboxylic oxime derivative according to claim 5,which is selected from any one of Table
 1. 7. A preparation method ofthe pyridyloxy carboxylic oxime derivative according to any one ofclaims 1-6, which comprises the following steps. a compound of formulaII is reacted with a compound of formula III to obtain a compound offormula I; the reaction scheme is as follows:

wherein, the reaction is carried out in the presence of a dehydrant anda solvent, preferably the dehydrant is DCC, and the solvent is one ormore selected from the group consisting of dichloromethane,dichloroethane, acetonitrile, N,N-dimethylformamide,N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene andxylene.
 8. A herbicidal composition comprising (i) at least one of thepyridyloxy carboxylic oxime derivatives according to any one of claims1-6; preferably, further comprising (ii) one or more further herbicidesand/or safeners; more preferably, further comprising (iii)agrochemically acceptable formulation auxiliaries.
 9. A method forcontrolling a weed comprising applying a herbicidally effective amountof at least one of the pyridyloxy carboxylic oxime derivatives accordingto any one of claims 1-6 or the herbicidal composition according toclaim 8 on a plant or in a weed area. Preferably, the plant is rice(such as japonica rice, indica rice); or the weed is a gramineous weed(such as Digitaria sanguinalis, Echinochloa crusgalli, Setaria viridis,Leptochloa chinensis), a broad-leaved weed (such as MonochoriaVaginalis, Galium spurium, Sagittaria trifolia, Murdannia triquetra) orcyperaceae weed (such as Cyperus iria, Scirpus juncoides).
 10. Use of atleast one of the pyridyloxy carboxylic oxime derivatives according toany one of claims 1-6 or the herbicidal composition according to claim 8for controlling a weed, preferably, the pyridyloxy carboxylic oximederivatives thereof being used to control a weed in a useful crop,wherein the useful crop is a genetically modified crop or a crop treatedby gene editing technology. Preferably, the crop is rice (such asjaponica rice, indica rice); or the weed is a gramineous weed (such asDigitaria sanguinalis, Echinochloa crusgalli, Setaria viridis,Leptochloa chinensis), a broad-leaved weed (such as MonochoriaVaginalis, Galium spurium, Sagittaria trifolia, Murdannia triquetra) orcyperaceae weed (such as Cyperus iria, Scirpus juncoides).